diff --git a/stdlib/@python2/BaseHTTPServer.pyi b/stdlib/@python2/BaseHTTPServer.pyi
index 28fc4de0409b..46946aa37c46 100644
--- a/stdlib/@python2/BaseHTTPServer.pyi
+++ b/stdlib/@python2/BaseHTTPServer.pyi
@@ -1,6 +1,6 @@
 import mimetools
 import SocketServer
-from typing import Any, BinaryIO, Callable, Mapping, Optional, Tuple, Union
+from typing import Any, BinaryIO, Callable, Mapping, Tuple
 
 class HTTPServer(SocketServer.TCPServer):
     server_name: str
@@ -27,15 +27,15 @@ class BaseHTTPRequestHandler(SocketServer.StreamRequestHandler):
     def __init__(self, request: bytes, client_address: Tuple[str, int], server: SocketServer.BaseServer) -> None: ...
     def handle(self) -> None: ...
     def handle_one_request(self) -> None: ...
-    def send_error(self, code: int, message: Optional[str] = ...) -> None: ...
-    def send_response(self, code: int, message: Optional[str] = ...) -> None: ...
+    def send_error(self, code: int, message: str | None = ...) -> None: ...
+    def send_response(self, code: int, message: str | None = ...) -> None: ...
     def send_header(self, keyword: str, value: str) -> None: ...
     def end_headers(self) -> None: ...
     def flush_headers(self) -> None: ...
-    def log_request(self, code: Union[int, str] = ..., size: Union[int, str] = ...) -> None: ...
+    def log_request(self, code: int | str = ..., size: int | str = ...) -> None: ...
     def log_error(self, format: str, *args: Any) -> None: ...
     def log_message(self, format: str, *args: Any) -> None: ...
     def version_string(self) -> str: ...
-    def date_time_string(self, timestamp: Optional[int] = ...) -> str: ...
+    def date_time_string(self, timestamp: int | None = ...) -> str: ...
     def log_date_time_string(self) -> str: ...
     def address_string(self) -> str: ...
diff --git a/stdlib/@python2/ConfigParser.pyi b/stdlib/@python2/ConfigParser.pyi
index 05c90ed2c248..89167b3e7ec8 100644
--- a/stdlib/@python2/ConfigParser.pyi
+++ b/stdlib/@python2/ConfigParser.pyi
@@ -1,5 +1,5 @@
 from _typeshed import SupportsNoArgReadline
-from typing import IO, Any, Dict, List, Optional, Sequence, Tuple, Union
+from typing import IO, Any, Dict, List, Sequence, Tuple
 
 DEFAULTSECT: str
 MAX_INTERPOLATION_DEPTH: int
@@ -65,7 +65,7 @@ class RawConfigParser:
     def add_section(self, section: str) -> None: ...
     def has_section(self, section: str) -> bool: ...
     def options(self, section: str) -> List[str]: ...
-    def read(self, filenames: Union[str, Sequence[str]]) -> List[str]: ...
+    def read(self, filenames: str | Sequence[str]) -> List[str]: ...
     def readfp(self, fp: SupportsNoArgReadline[str], filename: str = ...) -> None: ...
     def get(self, section: str, option: str) -> str: ...
     def items(self, section: str) -> List[Tuple[Any, Any]]: ...
@@ -84,8 +84,8 @@ class RawConfigParser:
 
 class ConfigParser(RawConfigParser):
     _KEYCRE: Any
-    def get(self, section: str, option: str, raw: bool = ..., vars: Optional[Dict[Any, Any]] = ...) -> Any: ...
-    def items(self, section: str, raw: bool = ..., vars: Optional[Dict[Any, Any]] = ...) -> List[Tuple[str, Any]]: ...
+    def get(self, section: str, option: str, raw: bool = ..., vars: Dict[Any, Any] | None = ...) -> Any: ...
+    def items(self, section: str, raw: bool = ..., vars: Dict[Any, Any] | None = ...) -> List[Tuple[str, Any]]: ...
     def _interpolate(self, section: str, option: str, rawval: Any, vars: Any) -> str: ...
     def _interpolation_replace(self, match: Any) -> str: ...
 
diff --git a/stdlib/@python2/Cookie.pyi b/stdlib/@python2/Cookie.pyi
index 91dd93221c73..3d01c3c66152 100644
--- a/stdlib/@python2/Cookie.pyi
+++ b/stdlib/@python2/Cookie.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Dict, Optional
+from typing import Any, Dict
 
 class CookieError(Exception): ...
 
@@ -10,17 +10,17 @@ class Morsel(Dict[Any, Any]):
     value: Any
     coded_value: Any
     def set(self, key, val, coded_val, LegalChars=..., idmap=..., translate=...): ...
-    def output(self, attrs: Optional[Any] = ..., header=...): ...
-    def js_output(self, attrs: Optional[Any] = ...): ...
-    def OutputString(self, attrs: Optional[Any] = ...): ...
+    def output(self, attrs: Any | None = ..., header=...): ...
+    def js_output(self, attrs: Any | None = ...): ...
+    def OutputString(self, attrs: Any | None = ...): ...
 
 class BaseCookie(Dict[Any, Any]):
     def value_decode(self, val): ...
     def value_encode(self, val): ...
-    def __init__(self, input: Optional[Any] = ...): ...
+    def __init__(self, input: Any | None = ...): ...
     def __setitem__(self, key, value): ...
-    def output(self, attrs: Optional[Any] = ..., header=..., sep=...): ...
-    def js_output(self, attrs: Optional[Any] = ...): ...
+    def output(self, attrs: Any | None = ..., header=..., sep=...): ...
+    def js_output(self, attrs: Any | None = ...): ...
     def load(self, rawdata): ...
 
 class SimpleCookie(BaseCookie):
@@ -28,12 +28,12 @@ class SimpleCookie(BaseCookie):
     def value_encode(self, val): ...
 
 class SerialCookie(BaseCookie):
-    def __init__(self, input: Optional[Any] = ...): ...
+    def __init__(self, input: Any | None = ...): ...
     def value_decode(self, val): ...
     def value_encode(self, val): ...
 
 class SmartCookie(BaseCookie):
-    def __init__(self, input: Optional[Any] = ...): ...
+    def __init__(self, input: Any | None = ...): ...
     def value_decode(self, val): ...
     def value_encode(self, val): ...
 
diff --git a/stdlib/@python2/Queue.pyi b/stdlib/@python2/Queue.pyi
index 5297a4b76034..24743a80280d 100644
--- a/stdlib/@python2/Queue.pyi
+++ b/stdlib/@python2/Queue.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Deque, Generic, Optional, TypeVar
+from typing import Any, Deque, Generic, TypeVar
 
 _T = TypeVar("_T")
 
@@ -19,9 +19,9 @@ class Queue(Generic[_T]):
     def qsize(self) -> int: ...
     def empty(self) -> bool: ...
     def full(self) -> bool: ...
-    def put(self, item: _T, block: bool = ..., timeout: Optional[float] = ...) -> None: ...
+    def put(self, item: _T, block: bool = ..., timeout: float | None = ...) -> None: ...
     def put_nowait(self, item: _T) -> None: ...
-    def get(self, block: bool = ..., timeout: Optional[float] = ...) -> _T: ...
+    def get(self, block: bool = ..., timeout: float | None = ...) -> _T: ...
     def get_nowait(self) -> _T: ...
 
 class PriorityQueue(Queue[_T]): ...
diff --git a/stdlib/@python2/SimpleHTTPServer.pyi b/stdlib/@python2/SimpleHTTPServer.pyi
index 7e62b49e8bc6..758d5bd6d515 100644
--- a/stdlib/@python2/SimpleHTTPServer.pyi
+++ b/stdlib/@python2/SimpleHTTPServer.pyi
@@ -1,14 +1,14 @@
 import BaseHTTPServer
 from StringIO import StringIO
-from typing import IO, Any, AnyStr, Mapping, Optional, Union
+from typing import IO, Any, AnyStr, Mapping
 
 class SimpleHTTPRequestHandler(BaseHTTPServer.BaseHTTPRequestHandler):
     server_version: str
     def do_GET(self) -> None: ...
     def do_HEAD(self) -> None: ...
-    def send_head(self) -> Optional[IO[str]]: ...
-    def list_directory(self, path: Union[str, unicode]) -> Optional[StringIO[Any]]: ...
+    def send_head(self) -> IO[str] | None: ...
+    def list_directory(self, path: str | unicode) -> StringIO[Any] | None: ...
     def translate_path(self, path: AnyStr) -> AnyStr: ...
     def copyfile(self, source: IO[AnyStr], outputfile: IO[AnyStr]): ...
-    def guess_type(self, path: Union[str, unicode]) -> str: ...
+    def guess_type(self, path: str | unicode) -> str: ...
     extensions_map: Mapping[str, str]
diff --git a/stdlib/@python2/SocketServer.pyi b/stdlib/@python2/SocketServer.pyi
index e7f84e7cb7a5..e5a19ffd5e68 100644
--- a/stdlib/@python2/SocketServer.pyi
+++ b/stdlib/@python2/SocketServer.pyi
@@ -1,6 +1,6 @@
 import sys
 from socket import SocketType
-from typing import Any, BinaryIO, Callable, ClassVar, List, Optional, Text, Tuple, Union
+from typing import Any, BinaryIO, Callable, ClassVar, List, Text, Tuple, Union
 
 class BaseServer:
     address_family: int
@@ -10,7 +10,7 @@ class BaseServer:
     allow_reuse_address: bool
     request_queue_size: int
     socket_type: int
-    timeout: Optional[float]
+    timeout: float | None
     def __init__(self, server_address: Any, RequestHandlerClass: Callable[..., BaseRequestHandler]) -> None: ...
     def fileno(self) -> int: ...
     def handle_request(self) -> None: ...
@@ -46,22 +46,22 @@ if sys.platform != "win32":
     class UnixStreamServer(BaseServer):
         def __init__(
             self,
-            server_address: Union[Text, bytes],
+            server_address: Text | bytes,
             RequestHandlerClass: Callable[..., BaseRequestHandler],
             bind_and_activate: bool = ...,
         ) -> None: ...
     class UnixDatagramServer(BaseServer):
         def __init__(
             self,
-            server_address: Union[Text, bytes],
+            server_address: Text | bytes,
             RequestHandlerClass: Callable[..., BaseRequestHandler],
             bind_and_activate: bool = ...,
         ) -> None: ...
 
 if sys.platform != "win32":
     class ForkingMixIn:
-        timeout: Optional[float]  # undocumented
-        active_children: Optional[List[int]]  # undocumented
+        timeout: float | None  # undocumented
+        active_children: List[int] | None  # undocumented
         max_children: int  # undocumented
         def collect_children(self) -> None: ...  # undocumented
         def handle_timeout(self) -> None: ...  # undocumented
@@ -101,7 +101,7 @@ class BaseRequestHandler:
 class StreamRequestHandler(BaseRequestHandler):
     rbufsize: ClassVar[int]  # undocumented
     wbufsize: ClassVar[int]  # undocumented
-    timeout: ClassVar[Optional[float]]  # undocumented
+    timeout: ClassVar[float | None]  # undocumented
     disable_nagle_algorithm: ClassVar[bool]  # undocumented
     connection: SocketType  # undocumented
     rfile: BinaryIO
diff --git a/stdlib/@python2/StringIO.pyi b/stdlib/@python2/StringIO.pyi
index 4470b4fc1ad0..efa90f8e0330 100644
--- a/stdlib/@python2/StringIO.pyi
+++ b/stdlib/@python2/StringIO.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, AnyStr, Generic, Iterable, Iterator, List, Optional
+from typing import IO, Any, AnyStr, Generic, Iterable, Iterator, List
 
 class StringIO(IO[AnyStr], Generic[AnyStr]):
     closed: bool
@@ -15,7 +15,7 @@ class StringIO(IO[AnyStr], Generic[AnyStr]):
     def read(self, n: int = ...) -> AnyStr: ...
     def readline(self, length: int = ...) -> AnyStr: ...
     def readlines(self, sizehint: int = ...) -> List[AnyStr]: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def write(self, s: AnyStr) -> int: ...
     def writelines(self, iterable: Iterable[AnyStr]) -> None: ...
     def flush(self) -> None: ...
diff --git a/stdlib/@python2/UserDict.pyi b/stdlib/@python2/UserDict.pyi
index afa07d861a9e..dce7bebafd66 100644
--- a/stdlib/@python2/UserDict.pyi
+++ b/stdlib/@python2/UserDict.pyi
@@ -1,19 +1,4 @@
-from typing import (
-    Any,
-    Container,
-    Dict,
-    Generic,
-    Iterable,
-    Iterator,
-    List,
-    Mapping,
-    Optional,
-    Sized,
-    Tuple,
-    TypeVar,
-    Union,
-    overload,
-)
+from typing import Any, Container, Dict, Generic, Iterable, Iterator, List, Mapping, Sized, Tuple, TypeVar, overload
 
 _KT = TypeVar("_KT")
 _VT = TypeVar("_VT")
@@ -33,9 +18,9 @@ class DictMixin(Iterable[_KT], Container[_KT], Sized, Generic[_KT, _VT]):
     # From  typing.Mapping[_KT, _VT]
     # (can't inherit because of keys())
     @overload
-    def get(self, k: _KT) -> Optional[_VT]: ...
+    def get(self, k: _KT) -> _VT | None: ...
     @overload
-    def get(self, k: _KT, default: Union[_VT, _T]) -> Union[_VT, _T]: ...
+    def get(self, k: _KT, default: _VT | _T) -> _VT | _T: ...
     def values(self) -> List[_VT]: ...
     def items(self) -> List[Tuple[_KT, _VT]]: ...
     def iterkeys(self) -> Iterator[_KT]: ...
diff --git a/stdlib/@python2/UserList.pyi b/stdlib/@python2/UserList.pyi
index 0fc2a31b8651..be4ebce5a815 100644
--- a/stdlib/@python2/UserList.pyi
+++ b/stdlib/@python2/UserList.pyi
@@ -1,4 +1,4 @@
-from typing import Iterable, List, MutableSequence, TypeVar, Union, overload
+from typing import Iterable, List, MutableSequence, TypeVar, overload
 
 _T = TypeVar("_T")
 _S = TypeVar("_S")
@@ -10,7 +10,7 @@ class UserList(MutableSequence[_T]):
     def __setitem__(self, i: int, o: _T) -> None: ...
     @overload
     def __setitem__(self, s: slice, o: Iterable[_T]) -> None: ...
-    def __delitem__(self, i: Union[int, slice]) -> None: ...
+    def __delitem__(self, i: int | slice) -> None: ...
     def __len__(self) -> int: ...
     @overload
     def __getitem__(self, i: int) -> _T: ...
diff --git a/stdlib/@python2/UserString.pyi b/stdlib/@python2/UserString.pyi
index 74ab34f6ac69..f60dbe18f9b1 100644
--- a/stdlib/@python2/UserString.pyi
+++ b/stdlib/@python2/UserString.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Iterable, List, MutableSequence, Optional, Sequence, Text, Tuple, TypeVar, Union, overload
+from typing import Any, Iterable, List, MutableSequence, Sequence, Text, Tuple, TypeVar, overload
 
 _UST = TypeVar("_UST", bound=UserString)
 _MST = TypeVar("_MST", bound=MutableString)
@@ -24,9 +24,9 @@ class UserString(Sequence[UserString]):
     def capitalize(self: _UST) -> _UST: ...
     def center(self: _UST, width: int, *args: Any) -> _UST: ...
     def count(self, sub: int, start: int = ..., end: int = ...) -> int: ...
-    def decode(self: _UST, encoding: Optional[str] = ..., errors: Optional[str] = ...) -> _UST: ...
-    def encode(self: _UST, encoding: Optional[str] = ..., errors: Optional[str] = ...) -> _UST: ...
-    def endswith(self, suffix: Union[Text, Tuple[Text, ...]], start: Optional[int] = ..., end: Optional[int] = ...) -> bool: ...
+    def decode(self: _UST, encoding: str | None = ..., errors: str | None = ...) -> _UST: ...
+    def encode(self: _UST, encoding: str | None = ..., errors: str | None = ...) -> _UST: ...
+    def endswith(self, suffix: Text | Tuple[Text, ...], start: int | None = ..., end: int | None = ...) -> bool: ...
     def expandtabs(self: _UST, tabsize: int = ...) -> _UST: ...
     def find(self, sub: Text, start: int = ..., end: int = ...) -> int: ...
     def index(self, sub: Text, start: int = ..., end: int = ...) -> int: ...
@@ -42,19 +42,19 @@ class UserString(Sequence[UserString]):
     def join(self, seq: Iterable[Text]) -> Text: ...
     def ljust(self: _UST, width: int, *args: Any) -> _UST: ...
     def lower(self: _UST) -> _UST: ...
-    def lstrip(self: _UST, chars: Optional[Text] = ...) -> _UST: ...
+    def lstrip(self: _UST, chars: Text | None = ...) -> _UST: ...
     def partition(self, sep: Text) -> Tuple[Text, Text, Text]: ...
     def replace(self: _UST, old: Text, new: Text, maxsplit: int = ...) -> _UST: ...
     def rfind(self, sub: Text, start: int = ..., end: int = ...) -> int: ...
     def rindex(self, sub: Text, start: int = ..., end: int = ...) -> int: ...
     def rjust(self: _UST, width: int, *args: Any) -> _UST: ...
     def rpartition(self, sep: Text) -> Tuple[Text, Text, Text]: ...
-    def rstrip(self: _UST, chars: Optional[Text] = ...) -> _UST: ...
-    def split(self, sep: Optional[Text] = ..., maxsplit: int = ...) -> List[Text]: ...
-    def rsplit(self, sep: Optional[Text] = ..., maxsplit: int = ...) -> List[Text]: ...
+    def rstrip(self: _UST, chars: Text | None = ...) -> _UST: ...
+    def split(self, sep: Text | None = ..., maxsplit: int = ...) -> List[Text]: ...
+    def rsplit(self, sep: Text | None = ..., maxsplit: int = ...) -> List[Text]: ...
     def splitlines(self, keepends: int = ...) -> List[Text]: ...
-    def startswith(self, prefix: Union[Text, Tuple[Text, ...]], start: Optional[int] = ..., end: Optional[int] = ...) -> bool: ...
-    def strip(self: _UST, chars: Optional[Text] = ...) -> _UST: ...
+    def startswith(self, prefix: Text | Tuple[Text, ...], start: int | None = ..., end: int | None = ...) -> bool: ...
+    def strip(self: _UST, chars: Text | None = ...) -> _UST: ...
     def swapcase(self: _UST) -> _UST: ...
     def title(self: _UST) -> _UST: ...
     def translate(self: _UST, *args: Any) -> _UST: ...
@@ -66,8 +66,8 @@ class MutableString(UserString, MutableSequence[MutableString]):
     def __getitem__(self: _MST, i: int) -> _MST: ...
     @overload
     def __getitem__(self: _MST, s: slice) -> _MST: ...
-    def __setitem__(self, index: Union[int, slice], sub: Any) -> None: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __setitem__(self, index: int | slice, sub: Any) -> None: ...
+    def __delitem__(self, index: int | slice) -> None: ...
     def immutable(self) -> UserString: ...
     def __iadd__(self: _MST, other: Any) -> _MST: ...
     def __imul__(self, n: int) -> _MST: ...
diff --git a/stdlib/@python2/__builtin__.pyi b/stdlib/@python2/__builtin__.pyi
index 0b2c89e8d80c..ebe9cdd95038 100644
--- a/stdlib/@python2/__builtin__.pyi
+++ b/stdlib/@python2/__builtin__.pyi
@@ -26,7 +26,6 @@ from typing import (
     MutableSequence,
     MutableSet,
     NoReturn,
-    Optional,
     Protocol,
     Reversible,
     Sequence,
@@ -40,7 +39,6 @@ from typing import (
     Tuple,
     Type,
     TypeVar,
-    Union,
     ValuesView,
     overload,
 )
@@ -66,9 +64,9 @@ _TT = TypeVar("_TT", bound="type")
 _TBE = TypeVar("_TBE", bound="BaseException")
 
 class object:
-    __doc__: Optional[str]
+    __doc__: str | None
     __dict__: Dict[str, Any]
-    __slots__: Union[Text, Iterable[Text]]
+    __slots__: Text | Iterable[Text]
     __module__: str
     @property
     def __class__(self: _T) -> Type[_T]: ...
@@ -86,20 +84,20 @@ class object:
     def __getattribute__(self, name: str) -> Any: ...
     def __delattr__(self, name: str) -> None: ...
     def __sizeof__(self) -> int: ...
-    def __reduce__(self) -> Union[str, Tuple[Any, ...]]: ...
-    def __reduce_ex__(self, protocol: int) -> Union[str, Tuple[Any, ...]]: ...
+    def __reduce__(self) -> str | Tuple[Any, ...]: ...
+    def __reduce_ex__(self, protocol: int) -> str | Tuple[Any, ...]: ...
 
 class staticmethod(object):  # Special, only valid as a decorator.
     __func__: Callable[..., Any]
     def __init__(self, f: Callable[..., Any]) -> None: ...
     def __new__(cls: Type[_T], *args: Any, **kwargs: Any) -> _T: ...
-    def __get__(self, obj: _T, type: Optional[Type[_T]] = ...) -> Callable[..., Any]: ...
+    def __get__(self, obj: _T, type: Type[_T] | None = ...) -> Callable[..., Any]: ...
 
 class classmethod(object):  # Special, only valid as a decorator.
     __func__: Callable[..., Any]
     def __init__(self, f: Callable[..., Any]) -> None: ...
     def __new__(cls: Type[_T], *args: Any, **kwargs: Any) -> _T: ...
-    def __get__(self, obj: _T, type: Optional[Type[_T]] = ...) -> Callable[..., Any]: ...
+    def __get__(self, obj: _T, type: Type[_T] | None = ...) -> Callable[..., Any]: ...
 
 class type(object):
     __base__: type
@@ -137,9 +135,9 @@ class super(object):
 
 class int:
     @overload
-    def __new__(cls: Type[_T], x: Union[Text, bytes, SupportsInt, _SupportsIndex, _SupportsTrunc] = ...) -> _T: ...
+    def __new__(cls: Type[_T], x: Text | bytes | SupportsInt | _SupportsIndex | _SupportsTrunc = ...) -> _T: ...
     @overload
-    def __new__(cls: Type[_T], x: Union[Text, bytes, bytearray], base: int) -> _T: ...
+    def __new__(cls: Type[_T], x: Text | bytes | bytearray, base: int) -> _T: ...
     @property
     def real(self) -> int: ...
     @property
@@ -167,10 +165,10 @@ class int:
     def __rmod__(self, x: int) -> int: ...
     def __rdivmod__(self, x: int) -> Tuple[int, int]: ...
     @overload
-    def __pow__(self, __x: Literal[2], __modulo: Optional[int] = ...) -> int: ...
+    def __pow__(self, __x: Literal[2], __modulo: int | None = ...) -> int: ...
     @overload
-    def __pow__(self, __x: int, __modulo: Optional[int] = ...) -> Any: ...  # Return type can be int or float, depending on x.
-    def __rpow__(self, x: int, mod: Optional[int] = ...) -> Any: ...
+    def __pow__(self, __x: int, __modulo: int | None = ...) -> Any: ...  # Return type can be int or float, depending on x.
+    def __rpow__(self, x: int, mod: int | None = ...) -> Any: ...
     def __and__(self, n: int) -> int: ...
     def __or__(self, n: int) -> int: ...
     def __xor__(self, n: int) -> int: ...
@@ -201,7 +199,7 @@ class int:
     def __index__(self) -> int: ...
 
 class float:
-    def __new__(cls: Type[_T], x: Union[SupportsFloat, _SupportsIndex, Text, bytes, bytearray] = ...) -> _T: ...
+    def __new__(cls: Type[_T], x: SupportsFloat | _SupportsIndex | Text | bytes | bytearray = ...) -> _T: ...
     def as_integer_ratio(self) -> Tuple[int, int]: ...
     def hex(self) -> str: ...
     def is_integer(self) -> bool: ...
@@ -253,7 +251,7 @@ class complex:
     @overload
     def __new__(cls: Type[_T], real: float = ..., imag: float = ...) -> _T: ...
     @overload
-    def __new__(cls: Type[_T], real: Union[str, SupportsComplex, _SupportsIndex]) -> _T: ...
+    def __new__(cls: Type[_T], real: str | SupportsComplex | _SupportsIndex) -> _T: ...
     @property
     def real(self) -> float: ...
     @property
@@ -295,9 +293,7 @@ class unicode(basestring, Sequence[unicode]):
     def count(self, x: unicode) -> int: ...
     def decode(self, encoding: unicode = ..., errors: unicode = ...) -> unicode: ...
     def encode(self, encoding: unicode = ..., errors: unicode = ...) -> str: ...
-    def endswith(
-        self, __suffix: Union[unicode, Tuple[unicode, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def endswith(self, __suffix: unicode | Tuple[unicode, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def expandtabs(self, tabsize: int = ...) -> unicode: ...
     def find(self, sub: unicode, start: int = ..., end: int = ...) -> int: ...
     def format(self, *args: object, **kwargs: object) -> unicode: ...
@@ -323,17 +319,15 @@ class unicode(basestring, Sequence[unicode]):
     def rindex(self, sub: unicode, start: int = ..., end: int = ...) -> int: ...
     def rjust(self, width: int, fillchar: unicode = ...) -> unicode: ...
     def rpartition(self, sep: unicode) -> Tuple[unicode, unicode, unicode]: ...
-    def rsplit(self, sep: Optional[unicode] = ..., maxsplit: int = ...) -> List[unicode]: ...
+    def rsplit(self, sep: unicode | None = ..., maxsplit: int = ...) -> List[unicode]: ...
     def rstrip(self, chars: unicode = ...) -> unicode: ...
-    def split(self, sep: Optional[unicode] = ..., maxsplit: int = ...) -> List[unicode]: ...
+    def split(self, sep: unicode | None = ..., maxsplit: int = ...) -> List[unicode]: ...
     def splitlines(self, keepends: bool = ...) -> List[unicode]: ...
-    def startswith(
-        self, __prefix: Union[unicode, Tuple[unicode, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def startswith(self, __prefix: unicode | Tuple[unicode, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def strip(self, chars: unicode = ...) -> unicode: ...
     def swapcase(self) -> unicode: ...
     def title(self) -> unicode: ...
-    def translate(self, table: Union[Dict[int, Any], unicode]) -> unicode: ...
+    def translate(self, table: Dict[int, Any] | unicode) -> unicode: ...
     def upper(self) -> unicode: ...
     def zfill(self, width: int) -> unicode: ...
     @overload
@@ -353,7 +347,7 @@ class unicode(basestring, Sequence[unicode]):
     def __ge__(self, x: unicode) -> bool: ...
     def __len__(self) -> int: ...
     # The argument type is incompatible with Sequence
-    def __contains__(self, s: Union[unicode, bytes]) -> bool: ...  # type: ignore
+    def __contains__(self, s: unicode | bytes) -> bool: ...  # type: ignore
     def __iter__(self) -> Iterator[unicode]: ...
     def __str__(self) -> str: ...
     def __repr__(self) -> str: ...
@@ -369,17 +363,15 @@ class str(Sequence[str], basestring):
     def __init__(self, o: object = ...) -> None: ...
     def capitalize(self) -> str: ...
     def center(self, __width: int, __fillchar: str = ...) -> str: ...
-    def count(self, x: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def count(self, x: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def decode(self, encoding: Text = ..., errors: Text = ...) -> unicode: ...
     def encode(self, encoding: Text = ..., errors: Text = ...) -> bytes: ...
-    def endswith(
-        self, __suffix: Union[Text, Tuple[Text, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def endswith(self, __suffix: Text | Tuple[Text, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def expandtabs(self, tabsize: int = ...) -> str: ...
-    def find(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def find(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def format(self, *args: object, **kwargs: object) -> str: ...
     def format_map(self, map: _FormatMapMapping) -> str: ...
-    def index(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def index(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def isalnum(self) -> bool: ...
     def isalpha(self) -> bool: ...
     def isdigit(self) -> bool: ...
@@ -401,8 +393,8 @@ class str(Sequence[str], basestring):
     @overload
     def partition(self, __sep: unicode) -> Tuple[unicode, unicode, unicode]: ...
     def replace(self, __old: AnyStr, __new: AnyStr, __count: int = ...) -> AnyStr: ...
-    def rfind(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
-    def rindex(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def rfind(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
+    def rindex(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def rjust(self, __width: int, __fillchar: str = ...) -> str: ...
     @overload
     def rpartition(self, __sep: bytearray) -> Tuple[str, bytearray, str]: ...
@@ -411,7 +403,7 @@ class str(Sequence[str], basestring):
     @overload
     def rpartition(self, __sep: unicode) -> Tuple[unicode, unicode, unicode]: ...
     @overload
-    def rsplit(self, sep: Optional[str] = ..., maxsplit: int = ...) -> List[str]: ...
+    def rsplit(self, sep: str | None = ..., maxsplit: int = ...) -> List[str]: ...
     @overload
     def rsplit(self, sep: unicode, maxsplit: int = ...) -> List[unicode]: ...
     @overload
@@ -419,28 +411,26 @@ class str(Sequence[str], basestring):
     @overload
     def rstrip(self, __chars: unicode) -> unicode: ...
     @overload
-    def split(self, sep: Optional[str] = ..., maxsplit: int = ...) -> List[str]: ...
+    def split(self, sep: str | None = ..., maxsplit: int = ...) -> List[str]: ...
     @overload
     def split(self, sep: unicode, maxsplit: int = ...) -> List[unicode]: ...
     def splitlines(self, keepends: bool = ...) -> List[str]: ...
-    def startswith(
-        self, __prefix: Union[Text, Tuple[Text, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def startswith(self, __prefix: Text | Tuple[Text, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     @overload
     def strip(self, __chars: str = ...) -> str: ...
     @overload
     def strip(self, chars: unicode) -> unicode: ...
     def swapcase(self) -> str: ...
     def title(self) -> str: ...
-    def translate(self, __table: Optional[AnyStr], deletechars: AnyStr = ...) -> AnyStr: ...
+    def translate(self, __table: AnyStr | None, deletechars: AnyStr = ...) -> AnyStr: ...
     def upper(self) -> str: ...
     def zfill(self, __width: int) -> str: ...
     def __add__(self, s: AnyStr) -> AnyStr: ...
     # Incompatible with Sequence.__contains__
-    def __contains__(self, o: Union[str, Text]) -> bool: ...  # type: ignore
+    def __contains__(self, o: str | Text) -> bool: ...  # type: ignore
     def __eq__(self, x: object) -> bool: ...
     def __ge__(self, x: Text) -> bool: ...
-    def __getitem__(self, i: Union[int, slice]) -> str: ...
+    def __getitem__(self, i: int | slice) -> str: ...
     def __gt__(self, x: Text) -> bool: ...
     def __hash__(self) -> int: ...
     def __iter__(self) -> Iterator[str]: ...
@@ -475,11 +465,9 @@ class bytearray(MutableSequence[int], ByteString):
     def center(self, __width: int, __fillchar: bytes = ...) -> bytearray: ...
     def count(self, __sub: str) -> int: ...
     def decode(self, encoding: Text = ..., errors: Text = ...) -> str: ...
-    def endswith(
-        self, __suffix: Union[bytes, Tuple[bytes, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def endswith(self, __suffix: bytes | Tuple[bytes, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def expandtabs(self, tabsize: int = ...) -> bytearray: ...
-    def extend(self, iterable: Union[str, Iterable[int]]) -> None: ...
+    def extend(self, iterable: str | Iterable[int]) -> None: ...
     def find(self, __sub: str, __start: int = ..., __end: int = ...) -> int: ...
     def index(self, __sub: str, __start: int = ..., __end: int = ...) -> int: ...
     def insert(self, __index: int, __item: int) -> None: ...
@@ -493,21 +481,19 @@ class bytearray(MutableSequence[int], ByteString):
     def join(self, __iterable: Iterable[str]) -> bytearray: ...
     def ljust(self, __width: int, __fillchar: str = ...) -> bytearray: ...
     def lower(self) -> bytearray: ...
-    def lstrip(self, __bytes: Optional[bytes] = ...) -> bytearray: ...
+    def lstrip(self, __bytes: bytes | None = ...) -> bytearray: ...
     def partition(self, __sep: bytes) -> Tuple[bytearray, bytearray, bytearray]: ...
     def replace(self, __old: bytes, __new: bytes, __count: int = ...) -> bytearray: ...
     def rfind(self, __sub: bytes, __start: int = ..., __end: int = ...) -> int: ...
     def rindex(self, __sub: bytes, __start: int = ..., __end: int = ...) -> int: ...
     def rjust(self, __width: int, __fillchar: bytes = ...) -> bytearray: ...
     def rpartition(self, __sep: bytes) -> Tuple[bytearray, bytearray, bytearray]: ...
-    def rsplit(self, sep: Optional[bytes] = ..., maxsplit: int = ...) -> List[bytearray]: ...
-    def rstrip(self, __bytes: Optional[bytes] = ...) -> bytearray: ...
-    def split(self, sep: Optional[bytes] = ..., maxsplit: int = ...) -> List[bytearray]: ...
+    def rsplit(self, sep: bytes | None = ..., maxsplit: int = ...) -> List[bytearray]: ...
+    def rstrip(self, __bytes: bytes | None = ...) -> bytearray: ...
+    def split(self, sep: bytes | None = ..., maxsplit: int = ...) -> List[bytearray]: ...
     def splitlines(self, keepends: bool = ...) -> List[bytearray]: ...
-    def startswith(
-        self, __prefix: Union[bytes, Tuple[bytes, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
-    def strip(self, __bytes: Optional[bytes] = ...) -> bytearray: ...
+    def startswith(self, __prefix: bytes | Tuple[bytes, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
+    def strip(self, __bytes: bytes | None = ...) -> bytearray: ...
     def swapcase(self) -> bytearray: ...
     def title(self) -> bytearray: ...
     def translate(self, __table: str) -> bytearray: ...
@@ -529,15 +515,15 @@ class bytearray(MutableSequence[int], ByteString):
     @overload
     def __setitem__(self, i: int, x: int) -> None: ...
     @overload
-    def __setitem__(self, s: slice, x: Union[Iterable[int], bytes]) -> None: ...
-    def __delitem__(self, i: Union[int, slice]) -> None: ...
+    def __setitem__(self, s: slice, x: Iterable[int] | bytes) -> None: ...
+    def __delitem__(self, i: int | slice) -> None: ...
     def __getslice__(self, start: int, stop: int) -> bytearray: ...
-    def __setslice__(self, start: int, stop: int, x: Union[Sequence[int], str]) -> None: ...
+    def __setslice__(self, start: int, stop: int, x: Sequence[int] | str) -> None: ...
     def __delslice__(self, start: int, stop: int) -> None: ...
     def __add__(self, s: bytes) -> bytearray: ...
     def __mul__(self, n: int) -> bytearray: ...
     # Incompatible with Sequence.__contains__
-    def __contains__(self, o: Union[int, bytes]) -> bool: ...  # type: ignore
+    def __contains__(self, o: int | bytes) -> bool: ...  # type: ignore
     def __eq__(self, x: object) -> bool: ...
     def __ne__(self, x: object) -> bool: ...
     def __lt__(self, x: bytes) -> bool: ...
@@ -548,9 +534,9 @@ class bytearray(MutableSequence[int], ByteString):
 class memoryview(Sized, Container[str]):
     format: str
     itemsize: int
-    shape: Optional[Tuple[int, ...]]
-    strides: Optional[Tuple[int, ...]]
-    suboffsets: Optional[Tuple[int, ...]]
+    shape: Tuple[int, ...] | None
+    strides: Tuple[int, ...] | None
+    suboffsets: Tuple[int, ...] | None
     readonly: bool
     ndim: int
     def __init__(self, obj: ReadableBuffer) -> None: ...
@@ -662,7 +648,7 @@ class list(MutableSequence[_T], Generic[_T]):
     def __setitem__(self, i: int, o: _T) -> None: ...
     @overload
     def __setitem__(self, s: slice, o: Iterable[_T]) -> None: ...
-    def __delitem__(self, i: Union[int, slice]) -> None: ...
+    def __delitem__(self, i: int | slice) -> None: ...
     def __getslice__(self, start: int, stop: int) -> List[_T]: ...
     def __setslice__(self, start: int, stop: int, o: Sequence[_T]) -> None: ...
     def __delslice__(self, start: int, stop: int) -> None: ...
@@ -743,18 +729,18 @@ class set(MutableSet[_T], Generic[_T]):
     def __str__(self) -> str: ...
     def __and__(self, s: AbstractSet[object]) -> Set[_T]: ...
     def __iand__(self, s: AbstractSet[object]) -> Set[_T]: ...
-    def __or__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
-    def __ior__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
+    def __or__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
+    def __ior__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
     @overload
-    def __sub__(self: Set[str], s: AbstractSet[Optional[Text]]) -> Set[_T]: ...
+    def __sub__(self: Set[str], s: AbstractSet[Text | None]) -> Set[_T]: ...
     @overload
-    def __sub__(self, s: AbstractSet[Optional[_T]]) -> Set[_T]: ...
+    def __sub__(self, s: AbstractSet[_T | None]) -> Set[_T]: ...
     @overload  # type: ignore
-    def __isub__(self: Set[str], s: AbstractSet[Optional[Text]]) -> Set[_T]: ...
+    def __isub__(self: Set[str], s: AbstractSet[Text | None]) -> Set[_T]: ...
     @overload
-    def __isub__(self, s: AbstractSet[Optional[_T]]) -> Set[_T]: ...
-    def __xor__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
-    def __ixor__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
+    def __isub__(self, s: AbstractSet[_T | None]) -> Set[_T]: ...
+    def __xor__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
+    def __ixor__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
     def __le__(self, s: AbstractSet[object]) -> bool: ...
     def __lt__(self, s: AbstractSet[object]) -> bool: ...
     def __ge__(self, s: AbstractSet[object]) -> bool: ...
@@ -776,9 +762,9 @@ class frozenset(AbstractSet[_T_co], Generic[_T_co]):
     def __iter__(self) -> Iterator[_T_co]: ...
     def __str__(self) -> str: ...
     def __and__(self, s: AbstractSet[_T_co]) -> FrozenSet[_T_co]: ...
-    def __or__(self, s: AbstractSet[_S]) -> FrozenSet[Union[_T_co, _S]]: ...
+    def __or__(self, s: AbstractSet[_S]) -> FrozenSet[_T_co | _S]: ...
     def __sub__(self, s: AbstractSet[_T_co]) -> FrozenSet[_T_co]: ...
-    def __xor__(self, s: AbstractSet[_S]) -> FrozenSet[Union[_T_co, _S]]: ...
+    def __xor__(self, s: AbstractSet[_S]) -> FrozenSet[_T_co | _S]: ...
     def __le__(self, s: AbstractSet[object]) -> bool: ...
     def __lt__(self, s: AbstractSet[object]) -> bool: ...
     def __ge__(self, s: AbstractSet[object]) -> bool: ...
@@ -802,15 +788,15 @@ class xrange(Sized, Iterable[int], Reversible[int]):
 class property(object):
     def __init__(
         self,
-        fget: Optional[Callable[[Any], Any]] = ...,
-        fset: Optional[Callable[[Any, Any], None]] = ...,
-        fdel: Optional[Callable[[Any], None]] = ...,
-        doc: Optional[str] = ...,
+        fget: Callable[[Any], Any] | None = ...,
+        fset: Callable[[Any, Any], None] | None = ...,
+        fdel: Callable[[Any], None] | None = ...,
+        doc: str | None = ...,
     ) -> None: ...
     def getter(self, fget: Callable[[Any], Any]) -> property: ...
     def setter(self, fset: Callable[[Any, Any], None]) -> property: ...
     def deleter(self, fdel: Callable[[Any], None]) -> property: ...
-    def __get__(self, obj: Any, type: Optional[type] = ...) -> Any: ...
+    def __get__(self, obj: Any, type: type | None = ...) -> Any: ...
     def __set__(self, obj: Any, value: Any) -> None: ...
     def __delete__(self, obj: Any) -> None: ...
     def fget(self) -> Any: ...
@@ -829,8 +815,8 @@ NotImplemented: _NotImplementedType
 def abs(__x: SupportsAbs[_T]) -> _T: ...
 def all(__iterable: Iterable[object]) -> bool: ...
 def any(__iterable: Iterable[object]) -> bool: ...
-def apply(__func: Callable[..., _T], __args: Optional[Sequence[Any]] = ..., __kwds: Optional[Mapping[str, Any]] = ...) -> _T: ...
-def bin(__number: Union[int, _SupportsIndex]) -> str: ...
+def apply(__func: Callable[..., _T], __args: Sequence[Any] | None = ..., __kwds: Mapping[str, Any] | None = ...) -> _T: ...
+def bin(__number: int | _SupportsIndex) -> str: ...
 def callable(__obj: object) -> bool: ...
 def chr(__i: int) -> str: ...
 def cmp(__x: Any, __y: Any) -> int: ...
@@ -838,7 +824,7 @@ def cmp(__x: Any, __y: Any) -> int: ...
 _N1 = TypeVar("_N1", bool, int, float, complex)
 
 def coerce(__x: _N1, __y: _N1) -> Tuple[_N1, _N1]: ...
-def compile(source: Union[Text, mod], filename: Text, mode: Text, flags: int = ..., dont_inherit: int = ...) -> Any: ...
+def compile(source: Text | mod, filename: Text, mode: Text, flags: int = ..., dont_inherit: int = ...) -> Any: ...
 def delattr(__obj: Any, __name: Text) -> None: ...
 def dir(__o: object = ...) -> List[str]: ...
 
@@ -846,18 +832,18 @@ _N2 = TypeVar("_N2", int, float)
 
 def divmod(__x: _N2, __y: _N2) -> Tuple[_N2, _N2]: ...
 def eval(
-    __source: Union[Text, bytes, CodeType], __globals: Optional[Dict[str, Any]] = ..., __locals: Optional[Mapping[str, Any]] = ...
+    __source: Text | bytes | CodeType, __globals: Dict[str, Any] | None = ..., __locals: Mapping[str, Any] | None = ...
 ) -> Any: ...
-def execfile(__filename: str, __globals: Optional[Dict[str, Any]] = ..., __locals: Optional[Dict[str, Any]] = ...) -> None: ...
+def execfile(__filename: str, __globals: Dict[str, Any] | None = ..., __locals: Dict[str, Any] | None = ...) -> None: ...
 def exit(code: object = ...) -> NoReturn: ...
 @overload
 def filter(__function: Callable[[AnyStr], Any], __iterable: AnyStr) -> AnyStr: ...  # type: ignore
 @overload
-def filter(__function: None, __iterable: Tuple[Optional[_T], ...]) -> Tuple[_T, ...]: ...  # type: ignore
+def filter(__function: None, __iterable: Tuple[_T | None, ...]) -> Tuple[_T, ...]: ...  # type: ignore
 @overload
 def filter(__function: Callable[[_T], Any], __iterable: Tuple[_T, ...]) -> Tuple[_T, ...]: ...  # type: ignore
 @overload
-def filter(__function: None, __iterable: Iterable[Optional[_T]]) -> List[_T]: ...
+def filter(__function: None, __iterable: Iterable[_T | None]) -> List[_T]: ...
 @overload
 def filter(__function: Callable[[_T], Any], __iterable: Iterable[_T]) -> List[_T]: ...
 def format(__value: object, __format_spec: str = ...) -> str: ...  # TODO unicode
@@ -867,26 +853,26 @@ def getattr(__o: Any, name: Text) -> Any: ...
 # While technically covered by the last overload, spelling out the types for None and bool
 # help mypy out in some tricky situations involving type context (aka bidirectional inference)
 @overload
-def getattr(__o: Any, name: Text, __default: None) -> Optional[Any]: ...
+def getattr(__o: Any, name: Text, __default: None) -> Any | None: ...
 @overload
-def getattr(__o: Any, name: Text, __default: bool) -> Union[Any, bool]: ...
+def getattr(__o: Any, name: Text, __default: bool) -> Any | bool: ...
 @overload
-def getattr(__o: Any, name: Text, __default: _T) -> Union[Any, _T]: ...
+def getattr(__o: Any, name: Text, __default: _T) -> Any | _T: ...
 def globals() -> Dict[str, Any]: ...
 def hasattr(__obj: Any, __name: Text) -> bool: ...
 def hash(__obj: object) -> int: ...
-def hex(__number: Union[int, _SupportsIndex]) -> str: ...
+def hex(__number: int | _SupportsIndex) -> str: ...
 def id(__obj: object) -> int: ...
 def input(__prompt: Any = ...) -> Any: ...
 def intern(__string: str) -> str: ...
 @overload
 def iter(__iterable: Iterable[_T]) -> Iterator[_T]: ...
 @overload
-def iter(__function: Callable[[], Optional[_T]], __sentinel: None) -> Iterator[_T]: ...
+def iter(__function: Callable[[], _T | None], __sentinel: None) -> Iterator[_T]: ...
 @overload
 def iter(__function: Callable[[], _T], __sentinel: Any) -> Iterator[_T]: ...
-def isinstance(__obj: object, __class_or_tuple: Union[type, Tuple[Union[type, Tuple[Any, ...]], ...]]) -> bool: ...
-def issubclass(__cls: type, __class_or_tuple: Union[type, Tuple[Union[type, Tuple[Any, ...]], ...]]) -> bool: ...
+def isinstance(__obj: object, __class_or_tuple: type | Tuple[type | Tuple[Any, ...], ...]) -> bool: ...
+def issubclass(__cls: type, __class_or_tuple: type | Tuple[type | Tuple[Any, ...], ...]) -> bool: ...
 def len(__obj: Sized) -> int: ...
 def locals() -> Dict[str, Any]: ...
 @overload
@@ -966,15 +952,13 @@ def min(__iterable: Iterable[_T], *, key: Callable[[_T], Any] = ...) -> _T: ...
 @overload
 def next(__i: Iterator[_T]) -> _T: ...
 @overload
-def next(__i: Iterator[_T], default: _VT) -> Union[_T, _VT]: ...
-def oct(__number: Union[int, _SupportsIndex]) -> str: ...
-def open(name: Union[unicode, int], mode: unicode = ..., buffering: int = ...) -> BinaryIO: ...
-def ord(__c: Union[Text, bytes]) -> int: ...
+def next(__i: Iterator[_T], default: _VT) -> _T | _VT: ...
+def oct(__number: int | _SupportsIndex) -> str: ...
+def open(name: unicode | int, mode: unicode = ..., buffering: int = ...) -> BinaryIO: ...
+def ord(__c: Text | bytes) -> int: ...
 
 # This is only available after from __future__ import print_function.
-def print(
-    *values: object, sep: Optional[Text] = ..., end: Optional[Text] = ..., file: Optional[SupportsWrite[Any]] = ...
-) -> None: ...
+def print(*values: object, sep: Text | None = ..., end: Text | None = ..., file: SupportsWrite[Any] | None = ...) -> None: ...
 
 _E = TypeVar("_E", contravariant=True)
 _M = TypeVar("_M", contravariant=True)
@@ -1018,12 +1002,12 @@ def round(number: SupportsFloat) -> float: ...
 def round(number: SupportsFloat, ndigits: int) -> float: ...
 def setattr(__obj: Any, __name: Text, __value: Any) -> None: ...
 def sorted(
-    __iterable: Iterable[_T], *, cmp: Callable[[_T, _T], int] = ..., key: Optional[Callable[[_T], Any]] = ..., reverse: bool = ...
+    __iterable: Iterable[_T], *, cmp: Callable[[_T, _T], int] = ..., key: Callable[[_T], Any] | None = ..., reverse: bool = ...
 ) -> List[_T]: ...
 @overload
-def sum(__iterable: Iterable[_T]) -> Union[_T, int]: ...
+def sum(__iterable: Iterable[_T]) -> _T | int: ...
 @overload
-def sum(__iterable: Iterable[_T], __start: _S) -> Union[_T, _S]: ...
+def sum(__iterable: Iterable[_T], __start: _S) -> _T | _S: ...
 def unichr(__i: int) -> unicode: ...
 def vars(__object: Any = ...) -> Dict[str, Any]: ...
 @overload
@@ -1052,8 +1036,8 @@ def zip(
 ) -> List[Tuple[Any, ...]]: ...
 def __import__(
     name: Text,
-    globals: Optional[Mapping[str, Any]] = ...,
-    locals: Optional[Mapping[str, Any]] = ...,
+    globals: Mapping[str, Any] | None = ...,
+    locals: Mapping[str, Any] | None = ...,
     fromlist: Sequence[str] = ...,
     level: int = ...,
 ) -> Any: ...
@@ -1071,7 +1055,7 @@ class buffer(Sized):
     def __init__(self, object: _AnyBuffer, offset: int = ..., size: int = ...) -> None: ...
     def __add__(self, other: _AnyBuffer) -> str: ...
     def __cmp__(self, other: _AnyBuffer) -> bool: ...
-    def __getitem__(self, key: Union[int, slice]) -> str: ...
+    def __getitem__(self, key: int | slice) -> str: ...
     def __getslice__(self, i: int, j: int) -> str: ...
     def __len__(self) -> int: ...
     def __mul__(self, x: int) -> str: ...
@@ -1119,10 +1103,10 @@ class RuntimeError(_StandardError): ...
 
 class SyntaxError(_StandardError):
     msg: str
-    lineno: Optional[int]
-    offset: Optional[int]
-    text: Optional[str]
-    filename: Optional[str]
+    lineno: int | None
+    offset: int | None
+    text: str | None
+    filename: str | None
 
 class SystemError(_StandardError): ...
 class TypeError(_StandardError): ...
@@ -1181,9 +1165,7 @@ class file(BinaryIO):
     def next(self) -> str: ...
     def read(self, n: int = ...) -> str: ...
     def __enter__(self) -> BinaryIO: ...
-    def __exit__(
-        self, t: Optional[type] = ..., exc: Optional[BaseException] = ..., tb: Optional[Any] = ...
-    ) -> Optional[bool]: ...
+    def __exit__(self, t: type | None = ..., exc: BaseException | None = ..., tb: Any | None = ...) -> bool | None: ...
     def flush(self) -> None: ...
     def fileno(self) -> int: ...
     def isatty(self) -> bool: ...
@@ -1197,4 +1179,4 @@ class file(BinaryIO):
     def readlines(self, hint: int = ...) -> List[str]: ...
     def write(self, data: str) -> int: ...
     def writelines(self, data: Iterable[str]) -> None: ...
-    def truncate(self, pos: Optional[int] = ...) -> int: ...
+    def truncate(self, pos: int | None = ...) -> int: ...
diff --git a/stdlib/@python2/_ast.pyi b/stdlib/@python2/_ast.pyi
index 4ca7def60b04..05cbc70c41d2 100644
--- a/stdlib/@python2/_ast.pyi
+++ b/stdlib/@python2/_ast.pyi
@@ -1,5 +1,4 @@
 import typing
-from typing import Optional
 
 __version__: str
 PyCF_ONLY_AST: int
@@ -41,7 +40,7 @@ class ClassDef(stmt):
     decorator_list: typing.List[expr]
 
 class Return(stmt):
-    value: Optional[expr]
+    value: expr | None
 
 class Delete(stmt):
     targets: typing.List[expr]
@@ -56,7 +55,7 @@ class AugAssign(stmt):
     value: expr
 
 class Print(stmt):
-    dest: Optional[expr]
+    dest: expr | None
     values: typing.List[expr]
     nl: bool
 
@@ -78,13 +77,13 @@ class If(stmt):
 
 class With(stmt):
     context_expr: expr
-    optional_vars: Optional[expr]
+    optional_vars: expr | None
     body: typing.List[stmt]
 
 class Raise(stmt):
-    type: Optional[expr]
-    inst: Optional[expr]
-    tback: Optional[expr]
+    type: expr | None
+    inst: expr | None
+    tback: expr | None
 
 class TryExcept(stmt):
     body: typing.List[stmt]
@@ -97,20 +96,20 @@ class TryFinally(stmt):
 
 class Assert(stmt):
     test: expr
-    msg: Optional[expr]
+    msg: expr | None
 
 class Import(stmt):
     names: typing.List[alias]
 
 class ImportFrom(stmt):
-    module: Optional[_identifier]
+    module: _identifier | None
     names: typing.List[alias]
-    level: Optional[int]
+    level: int | None
 
 class Exec(stmt):
     body: expr
-    globals: Optional[expr]
-    locals: Optional[expr]
+    globals: expr | None
+    locals: expr | None
 
 class Global(stmt):
     names: typing.List[_identifier]
@@ -126,9 +125,9 @@ class slice(AST): ...
 _slice = slice  # this lets us type the variable named 'slice' below
 
 class Slice(slice):
-    lower: Optional[expr]
-    upper: Optional[expr]
-    step: Optional[expr]
+    lower: expr | None
+    upper: expr | None
+    step: expr | None
 
 class ExtSlice(slice):
     dims: typing.List[slice]
@@ -189,7 +188,7 @@ class GeneratorExp(expr):
     generators: typing.List[comprehension]
 
 class Yield(expr):
-    value: Optional[expr]
+    value: expr | None
 
 class Compare(expr):
     left: expr
@@ -200,8 +199,8 @@ class Call(expr):
     func: expr
     args: typing.List[expr]
     keywords: typing.List[keyword]
-    starargs: Optional[expr]
-    kwargs: Optional[expr]
+    starargs: expr | None
+    kwargs: expr | None
 
 class Repr(expr):
     value: expr
@@ -282,16 +281,16 @@ class comprehension(AST):
 class excepthandler(AST): ...
 
 class ExceptHandler(excepthandler):
-    type: Optional[expr]
-    name: Optional[expr]
+    type: expr | None
+    name: expr | None
     body: typing.List[stmt]
     lineno: int
     col_offset: int
 
 class arguments(AST):
     args: typing.List[expr]
-    vararg: Optional[_identifier]
-    kwarg: Optional[_identifier]
+    vararg: _identifier | None
+    kwarg: _identifier | None
     defaults: typing.List[expr]
 
 class keyword(AST):
@@ -300,4 +299,4 @@ class keyword(AST):
 
 class alias(AST):
     name: _identifier
-    asname: Optional[_identifier]
+    asname: _identifier | None
diff --git a/stdlib/@python2/_bisect.pyi b/stdlib/@python2/_bisect.pyi
index 1e909c2a77d3..e3327a0af4e6 100644
--- a/stdlib/@python2/_bisect.pyi
+++ b/stdlib/@python2/_bisect.pyi
@@ -1,8 +1,8 @@
-from typing import MutableSequence, Optional, Sequence, TypeVar
+from typing import MutableSequence, Sequence, TypeVar
 
 _T = TypeVar("_T")
 
-def bisect_left(a: Sequence[_T], x: _T, lo: int = ..., hi: Optional[int] = ...) -> int: ...
-def bisect_right(a: Sequence[_T], x: _T, lo: int = ..., hi: Optional[int] = ...) -> int: ...
-def insort_left(a: MutableSequence[_T], x: _T, lo: int = ..., hi: Optional[int] = ...) -> None: ...
-def insort_right(a: MutableSequence[_T], x: _T, lo: int = ..., hi: Optional[int] = ...) -> None: ...
+def bisect_left(a: Sequence[_T], x: _T, lo: int = ..., hi: int | None = ...) -> int: ...
+def bisect_right(a: Sequence[_T], x: _T, lo: int = ..., hi: int | None = ...) -> int: ...
+def insort_left(a: MutableSequence[_T], x: _T, lo: int = ..., hi: int | None = ...) -> None: ...
+def insort_right(a: MutableSequence[_T], x: _T, lo: int = ..., hi: int | None = ...) -> None: ...
diff --git a/stdlib/@python2/_codecs.pyi b/stdlib/@python2/_codecs.pyi
index 70f7da857f5a..83601f6621bb 100644
--- a/stdlib/@python2/_codecs.pyi
+++ b/stdlib/@python2/_codecs.pyi
@@ -1,6 +1,6 @@
 import codecs
 import sys
-from typing import Any, Callable, Dict, Optional, Text, Tuple, Union
+from typing import Any, Callable, Dict, Text, Tuple, Union
 
 # For convenience:
 _Handler = Callable[[Exception], Tuple[Text, int]]
@@ -16,17 +16,17 @@ class _EncodingMap(object):
 _MapT = Union[Dict[int, int], _EncodingMap]
 
 def register(__search_function: Callable[[str], Any]) -> None: ...
-def register_error(__errors: Union[str, Text], __handler: _Handler) -> None: ...
-def lookup(__encoding: Union[str, Text]) -> codecs.CodecInfo: ...
-def lookup_error(__name: Union[str, Text]) -> _Handler: ...
-def decode(obj: Any, encoding: Union[str, Text] = ..., errors: _Errors = ...) -> Any: ...
-def encode(obj: Any, encoding: Union[str, Text] = ..., errors: _Errors = ...) -> Any: ...
+def register_error(__errors: str | Text, __handler: _Handler) -> None: ...
+def lookup(__encoding: str | Text) -> codecs.CodecInfo: ...
+def lookup_error(__name: str | Text) -> _Handler: ...
+def decode(obj: Any, encoding: str | Text = ..., errors: _Errors = ...) -> Any: ...
+def encode(obj: Any, encoding: str | Text = ..., errors: _Errors = ...) -> Any: ...
 def charmap_build(__map: Text) -> _MapT: ...
 def ascii_decode(__data: _Decodable, __errors: _Errors = ...) -> Tuple[Text, int]: ...
 def ascii_encode(__str: _Encodable, __errors: _Errors = ...) -> Tuple[bytes, int]: ...
 def charbuffer_encode(__data: _Encodable, __errors: _Errors = ...) -> Tuple[bytes, int]: ...
-def charmap_decode(__data: _Decodable, __errors: _Errors = ..., __mapping: Optional[_MapT] = ...) -> Tuple[Text, int]: ...
-def charmap_encode(__str: _Encodable, __errors: _Errors = ..., __mapping: Optional[_MapT] = ...) -> Tuple[bytes, int]: ...
+def charmap_decode(__data: _Decodable, __errors: _Errors = ..., __mapping: _MapT | None = ...) -> Tuple[Text, int]: ...
+def charmap_encode(__str: _Encodable, __errors: _Errors = ..., __mapping: _MapT | None = ...) -> Tuple[bytes, int]: ...
 def escape_decode(__data: _String, __errors: _Errors = ...) -> Tuple[str, int]: ...
 def escape_encode(__data: bytes, __errors: _Errors = ...) -> Tuple[bytes, int]: ...
 def latin_1_decode(__data: _Decodable, __errors: _Errors = ...) -> Tuple[Text, int]: ...
diff --git a/stdlib/@python2/_collections.pyi b/stdlib/@python2/_collections.pyi
index f97b6d5d6dd1..22ada07d0f24 100644
--- a/stdlib/@python2/_collections.pyi
+++ b/stdlib/@python2/_collections.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, Dict, Generic, Iterator, Optional, TypeVar, Union
+from typing import Any, Callable, Dict, Generic, Iterator, TypeVar
 
 _K = TypeVar("_K")
 _V = TypeVar("_V")
@@ -13,7 +13,7 @@ class defaultdict(Dict[_K, _V]):
     def copy(self: _T) -> _T: ...
 
 class deque(Generic[_T]):
-    maxlen: Optional[int]
+    maxlen: int | None
     def __init__(self, iterable: Iterator[_T] = ..., maxlen: int = ...) -> None: ...
     def append(self, x: _T) -> None: ...
     def appendleft(self, x: _T) -> None: ...
@@ -29,7 +29,7 @@ class deque(Generic[_T]):
     def __contains__(self, o: Any) -> bool: ...
     def __copy__(self) -> deque[_T]: ...
     def __getitem__(self, i: int) -> _T: ...
-    def __iadd__(self, other: deque[_T2]) -> deque[Union[_T, _T2]]: ...
+    def __iadd__(self, other: deque[_T2]) -> deque[_T | _T2]: ...
     def __iter__(self) -> Iterator[_T]: ...
     def __len__(self) -> int: ...
     def __reversed__(self) -> Iterator[_T]: ...
diff --git a/stdlib/@python2/_csv.pyi b/stdlib/@python2/_csv.pyi
index e194cc625889..ebe44bab67d9 100644
--- a/stdlib/@python2/_csv.pyi
+++ b/stdlib/@python2/_csv.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Iterable, Iterator, List, Optional, Protocol, Sequence, Text, Type, Union
+from typing import Any, Iterable, Iterator, List, Protocol, Sequence, Text, Type, Union
 
 QUOTE_ALL: int
 QUOTE_MINIMAL: int
@@ -9,8 +9,8 @@ class Error(Exception): ...
 
 class Dialect:
     delimiter: str
-    quotechar: Optional[str]
-    escapechar: Optional[str]
+    quotechar: str | None
+    escapechar: str | None
     doublequote: bool
     skipinitialspace: bool
     lineterminator: str
diff --git a/stdlib/@python2/_curses.pyi b/stdlib/@python2/_curses.pyi
index d6c286e37d13..32c1f761ac9e 100644
--- a/stdlib/@python2/_curses.pyi
+++ b/stdlib/@python2/_curses.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, BinaryIO, Optional, Tuple, Union, overload
+from typing import IO, Any, BinaryIO, Tuple, Union, overload
 
 _chtype = Union[str, bytes, int]
 
@@ -319,7 +319,7 @@ def resize_term(__nlines: int, __ncols: int) -> None: ...
 def resizeterm(__nlines: int, __ncols: int) -> None: ...
 def savetty() -> None: ...
 def setsyx(__y: int, __x: int) -> None: ...
-def setupterm(term: Optional[str] = ..., fd: int = ...) -> None: ...
+def setupterm(term: str | None = ..., fd: int = ...) -> None: ...
 def start_color() -> None: ...
 def termattrs() -> int: ...
 def termname() -> bytes: ...
diff --git a/stdlib/@python2/_dummy_threading.pyi b/stdlib/@python2/_dummy_threading.pyi
index bab2acdc84cd..e45a1b5c4a89 100644
--- a/stdlib/@python2/_dummy_threading.pyi
+++ b/stdlib/@python2/_dummy_threading.pyi
@@ -1,5 +1,5 @@
 from types import FrameType, TracebackType
-from typing import Any, Callable, Iterable, List, Mapping, Optional, Text, Type, TypeVar, Union
+from typing import Any, Callable, Iterable, List, Mapping, Optional, Text, Type, TypeVar
 
 # TODO recursive type
 _TF = Callable[[FrameType, str, Any], Optional[Callable[..., Any]]]
@@ -15,7 +15,7 @@ def current_thread() -> Thread: ...
 def currentThread() -> Thread: ...
 def enumerate() -> List[Thread]: ...
 def settrace(func: _TF) -> None: ...
-def setprofile(func: Optional[_PF]) -> None: ...
+def setprofile(func: _PF | None) -> None: ...
 def stack_size(size: int = ...) -> int: ...
 
 class ThreadError(Exception): ...
@@ -27,19 +27,19 @@ class local(object):
 
 class Thread:
     name: str
-    ident: Optional[int]
+    ident: int | None
     daemon: bool
     def __init__(
         self,
         group: None = ...,
-        target: Optional[Callable[..., Any]] = ...,
-        name: Optional[Text] = ...,
+        target: Callable[..., Any] | None = ...,
+        name: Text | None = ...,
         args: Iterable[Any] = ...,
-        kwargs: Optional[Mapping[Text, Any]] = ...,
+        kwargs: Mapping[Text, Any] | None = ...,
     ) -> None: ...
     def start(self) -> None: ...
     def run(self) -> None: ...
-    def join(self, timeout: Optional[float] = ...) -> None: ...
+    def join(self, timeout: float | None = ...) -> None: ...
     def getName(self) -> str: ...
     def setName(self, name: Text) -> None: ...
     def is_alive(self) -> bool: ...
@@ -53,8 +53,8 @@ class Lock:
     def __init__(self) -> None: ...
     def __enter__(self) -> bool: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
     def locked(self) -> bool: ...
@@ -63,22 +63,22 @@ class _RLock:
     def __init__(self) -> None: ...
     def __enter__(self) -> bool: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
 
 RLock = _RLock
 
 class Condition:
-    def __init__(self, lock: Union[Lock, _RLock, None] = ...) -> None: ...
+    def __init__(self, lock: Lock | _RLock | None = ...) -> None: ...
     def __enter__(self) -> bool: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
-    def wait(self, timeout: Optional[float] = ...) -> bool: ...
+    def wait(self, timeout: float | None = ...) -> bool: ...
     def notify(self, n: int = ...) -> None: ...
     def notify_all(self) -> None: ...
     def notifyAll(self) -> None: ...
@@ -86,8 +86,8 @@ class Condition:
 class Semaphore:
     def __init__(self, value: int = ...) -> None: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def __enter__(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
@@ -100,7 +100,7 @@ class Event:
     def isSet(self) -> bool: ...
     def set(self) -> None: ...
     def clear(self) -> None: ...
-    def wait(self, timeout: Optional[float] = ...) -> bool: ...
+    def wait(self, timeout: float | None = ...) -> bool: ...
 
 class Timer(Thread):
     def __init__(
diff --git a/stdlib/@python2/_heapq.pyi b/stdlib/@python2/_heapq.pyi
index f02fc470df14..08a8add08e9a 100644
--- a/stdlib/@python2/_heapq.pyi
+++ b/stdlib/@python2/_heapq.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, Iterable, List, Optional, TypeVar
+from typing import Any, Callable, Iterable, List, TypeVar
 
 _T = TypeVar("_T")
 
@@ -7,5 +7,5 @@ def heappop(__heap: List[_T]) -> _T: ...
 def heappush(__heap: List[_T], __item: _T) -> None: ...
 def heappushpop(__heap: List[_T], __item: _T) -> _T: ...
 def heapreplace(__heap: List[_T], __item: _T) -> _T: ...
-def nlargest(__n: int, __iterable: Iterable[_T], __key: Optional[Callable[[_T], Any]] = ...) -> List[_T]: ...
-def nsmallest(__n: int, __iterable: Iterable[_T], __key: Optional[Callable[[_T], Any]] = ...) -> List[_T]: ...
+def nlargest(__n: int, __iterable: Iterable[_T], __key: Callable[[_T], Any] | None = ...) -> List[_T]: ...
+def nsmallest(__n: int, __iterable: Iterable[_T], __key: Callable[[_T], Any] | None = ...) -> List[_T]: ...
diff --git a/stdlib/@python2/_io.pyi b/stdlib/@python2/_io.pyi
index 2d825b07bb85..fedbbe137940 100644
--- a/stdlib/@python2/_io.pyi
+++ b/stdlib/@python2/_io.pyi
@@ -1,6 +1,6 @@
 from _typeshed import Self
 from mmap import mmap
-from typing import IO, Any, BinaryIO, Iterable, List, Optional, Text, TextIO, Tuple, Type, TypeVar, Union
+from typing import IO, Any, BinaryIO, Iterable, List, Text, TextIO, Tuple, Type, TypeVar, Union
 
 _bytearray_like = Union[bytearray, mmap]
 
@@ -16,7 +16,7 @@ _T = TypeVar("_T")
 class _IOBase(BinaryIO):
     @property
     def closed(self) -> bool: ...
-    def _checkClosed(self, msg: Optional[str] = ...) -> None: ...  # undocumented
+    def _checkClosed(self, msg: str | None = ...) -> None: ...  # undocumented
     def _checkReadable(self) -> None: ...
     def _checkSeekable(self) -> None: ...
     def _checkWritable(self) -> None: ...
@@ -29,12 +29,10 @@ class _IOBase(BinaryIO):
     def seek(self, offset: int, whence: int = ...) -> int: ...
     def seekable(self) -> bool: ...
     def tell(self) -> int: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def writable(self) -> bool: ...
     def __enter__(self: Self) -> Self: ...
-    def __exit__(
-        self, t: Optional[Type[BaseException]], value: Optional[BaseException], traceback: Optional[Any]
-    ) -> Optional[bool]: ...
+    def __exit__(self, t: Type[BaseException] | None, value: BaseException | None, traceback: Any | None) -> bool | None: ...
     def __iter__(self: _T) -> _T: ...
     # The parameter type of writelines[s]() is determined by that of write():
     def writelines(self, lines: Iterable[bytes]) -> None: ...
@@ -100,12 +98,12 @@ class _RawIOBase(_IOBase):
 class FileIO(_RawIOBase, BytesIO):
     mode: str
     closefd: bool
-    def __init__(self, file: Union[str, int], mode: str = ..., closefd: bool = ...) -> None: ...
+    def __init__(self, file: str | int, mode: str = ..., closefd: bool = ...) -> None: ...
     def readinto(self, buffer: _bytearray_like) -> int: ...
     def write(self, pbuf: str) -> int: ...
 
 class IncrementalNewlineDecoder(object):
-    newlines: Union[str, unicode]
+    newlines: str | unicode
     def __init__(self, decoder, translate, z=...) -> None: ...
     def decode(self, input, final) -> Any: ...
     def getstate(self) -> Tuple[Any, int]: ...
@@ -114,9 +112,9 @@ class IncrementalNewlineDecoder(object):
 
 # Note: In the actual _io.py, _TextIOBase inherits from _IOBase.
 class _TextIOBase(TextIO):
-    errors: Optional[str]
+    errors: str | None
     # TODO: On _TextIOBase, this is always None. But it's unicode/bytes in subclasses.
-    newlines: Union[None, unicode, bytes]
+    newlines: None | unicode | bytes
     encoding: str
     @property
     def closed(self) -> bool: ...
@@ -137,19 +135,17 @@ class _TextIOBase(TextIO):
     def seek(self, offset: int, whence: int = ...) -> int: ...
     def seekable(self) -> bool: ...
     def tell(self) -> int: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def writable(self) -> bool: ...
     def write(self, pbuf: unicode) -> int: ...
     def writelines(self, lines: Iterable[unicode]) -> None: ...
     def __enter__(self: Self) -> Self: ...
-    def __exit__(
-        self, t: Optional[Type[BaseException]], value: Optional[BaseException], traceback: Optional[Any]
-    ) -> Optional[bool]: ...
+    def __exit__(self, t: Type[BaseException] | None, value: BaseException | None, traceback: Any | None) -> bool | None: ...
     def __iter__(self: _T) -> _T: ...
 
 class StringIO(_TextIOBase):
     line_buffering: bool
-    def __init__(self, initial_value: Optional[unicode] = ..., newline: Optional[unicode] = ...) -> None: ...
+    def __init__(self, initial_value: unicode | None = ..., newline: unicode | None = ...) -> None: ...
     def __setstate__(self, state: Tuple[Any, ...]) -> None: ...
     def __getstate__(self) -> Tuple[Any, ...]: ...
     # StringIO does not contain a "name" field. This workaround is necessary
@@ -166,19 +162,19 @@ class TextIOWrapper(_TextIOBase):
     def __init__(
         self,
         buffer: IO[Any],
-        encoding: Optional[Text] = ...,
-        errors: Optional[Text] = ...,
-        newline: Optional[Text] = ...,
+        encoding: Text | None = ...,
+        errors: Text | None = ...,
+        newline: Text | None = ...,
         line_buffering: bool = ...,
         write_through: bool = ...,
     ) -> None: ...
 
 def open(
-    file: Union[str, unicode, int],
+    file: str | unicode | int,
     mode: Text = ...,
     buffering: int = ...,
-    encoding: Optional[Text] = ...,
-    errors: Optional[Text] = ...,
-    newline: Optional[Text] = ...,
+    encoding: Text | None = ...,
+    errors: Text | None = ...,
+    newline: Text | None = ...,
     closefd: bool = ...,
 ) -> IO[Any]: ...
diff --git a/stdlib/@python2/_msi.pyi b/stdlib/@python2/_msi.pyi
index a8f9c60bbadd..a1030a66160f 100644
--- a/stdlib/@python2/_msi.pyi
+++ b/stdlib/@python2/_msi.pyi
@@ -1,11 +1,11 @@
 import sys
-from typing import List, Optional, Union
+from typing import List
 
 if sys.platform == "win32":
 
     # Actual typename View, not exposed by the implementation
     class _View:
-        def Execute(self, params: Optional[_Record] = ...) -> None: ...
+        def Execute(self, params: _Record | None = ...) -> None: ...
         def GetColumnInfo(self, kind: int) -> _Record: ...
         def Fetch(self) -> _Record: ...
         def Modify(self, mode: int, record: _Record) -> None: ...
@@ -15,9 +15,9 @@ if sys.platform == "win32":
         __init__: None  # type: ignore
     # Actual typename Summary, not exposed by the implementation
     class _Summary:
-        def GetProperty(self, propid: int) -> Optional[Union[str, bytes]]: ...
+        def GetProperty(self, propid: int) -> str | bytes | None: ...
         def GetPropertyCount(self) -> int: ...
-        def SetProperty(self, propid: int, value: Union[str, bytes]) -> None: ...
+        def SetProperty(self, propid: int, value: str | bytes) -> None: ...
         def Persist(self) -> None: ...
         # Don't exist at runtime
         __new__: None  # type: ignore
diff --git a/stdlib/@python2/_osx_support.pyi b/stdlib/@python2/_osx_support.pyi
index 5d67d996b30a..1b890d8d8a0a 100644
--- a/stdlib/@python2/_osx_support.pyi
+++ b/stdlib/@python2/_osx_support.pyi
@@ -1,4 +1,4 @@
-from typing import Dict, Iterable, List, Optional, Sequence, Tuple, TypeVar, Union
+from typing import Dict, Iterable, List, Sequence, Tuple, TypeVar
 
 _T = TypeVar("_T")
 _K = TypeVar("_K")
@@ -10,11 +10,11 @@ _UNIVERSAL_CONFIG_VARS: Tuple[str, ...]  # undocumented
 _COMPILER_CONFIG_VARS: Tuple[str, ...]  # undocumented
 _INITPRE: str  # undocumented
 
-def _find_executable(executable: str, path: Optional[str] = ...) -> Optional[str]: ...  # undocumented
-def _read_output(commandstring: str) -> Optional[str]: ...  # undocumented
+def _find_executable(executable: str, path: str | None = ...) -> str | None: ...  # undocumented
+def _read_output(commandstring: str) -> str | None: ...  # undocumented
 def _find_build_tool(toolname: str) -> str: ...  # undocumented
 
-_SYSTEM_VERSION: Optional[str]  # undocumented
+_SYSTEM_VERSION: str | None  # undocumented
 
 def _get_system_version() -> str: ...  # undocumented
 def _remove_original_values(_config_vars: Dict[str, str]) -> None: ...  # undocumented
@@ -30,4 +30,4 @@ def customize_config_vars(_config_vars: Dict[str, str]) -> Dict[str, str]: ...
 def customize_compiler(_config_vars: Dict[str, str]) -> Dict[str, str]: ...
 def get_platform_osx(
     _config_vars: Dict[str, str], osname: _T, release: _K, machine: _V
-) -> Tuple[Union[str, _T], Union[str, _K], Union[str, _V]]: ...
+) -> Tuple[str | _T, str | _K, str | _V]: ...
diff --git a/stdlib/@python2/_sha256.pyi b/stdlib/@python2/_sha256.pyi
index b6eb47d4bc83..746432094bf2 100644
--- a/stdlib/@python2/_sha256.pyi
+++ b/stdlib/@python2/_sha256.pyi
@@ -1,11 +1,9 @@
-from typing import Optional
-
 class sha224(object):
     name: str
     block_size: int
     digest_size: int
     digestsize: int
-    def __init__(self, init: Optional[str]) -> None: ...
+    def __init__(self, init: str | None) -> None: ...
     def copy(self) -> sha224: ...
     def digest(self) -> str: ...
     def hexdigest(self) -> str: ...
@@ -16,7 +14,7 @@ class sha256(object):
     block_size: int
     digest_size: int
     digestsize: int
-    def __init__(self, init: Optional[str]) -> None: ...
+    def __init__(self, init: str | None) -> None: ...
     def copy(self) -> sha256: ...
     def digest(self) -> str: ...
     def hexdigest(self) -> str: ...
diff --git a/stdlib/@python2/_sha512.pyi b/stdlib/@python2/_sha512.pyi
index b1ca9aee004c..90e2aee1542f 100644
--- a/stdlib/@python2/_sha512.pyi
+++ b/stdlib/@python2/_sha512.pyi
@@ -1,11 +1,9 @@
-from typing import Optional
-
 class sha384(object):
     name: str
     block_size: int
     digest_size: int
     digestsize: int
-    def __init__(self, init: Optional[str]) -> None: ...
+    def __init__(self, init: str | None) -> None: ...
     def copy(self) -> sha384: ...
     def digest(self) -> str: ...
     def hexdigest(self) -> str: ...
@@ -16,7 +14,7 @@ class sha512(object):
     block_size: int
     digest_size: int
     digestsize: int
-    def __init__(self, init: Optional[str]) -> None: ...
+    def __init__(self, init: str | None) -> None: ...
     def copy(self) -> sha512: ...
     def digest(self) -> str: ...
     def hexdigest(self) -> str: ...
diff --git a/stdlib/@python2/_socket.pyi b/stdlib/@python2/_socket.pyi
index 61c0def50587..c505384c5226 100644
--- a/stdlib/@python2/_socket.pyi
+++ b/stdlib/@python2/_socket.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, Optional, Tuple, Union, overload
+from typing import IO, Any, Tuple, overload
 
 AF_APPLETALK: int
 AF_ASH: int
@@ -276,6 +276,6 @@ class SocketType(object):
     @overload
     def sendto(self, data: str, flags: int, address: Tuple[Any, ...]) -> int: ...
     def setblocking(self, flag: bool) -> None: ...
-    def setsockopt(self, level: int, option: int, value: Union[int, str]) -> None: ...
-    def settimeout(self, value: Optional[float]) -> None: ...
+    def setsockopt(self, level: int, option: int, value: int | str) -> None: ...
+    def settimeout(self, value: float | None) -> None: ...
     def shutdown(self, flag: int) -> None: ...
diff --git a/stdlib/@python2/_sre.pyi b/stdlib/@python2/_sre.pyi
index 263f1da05632..3bacc097451e 100644
--- a/stdlib/@python2/_sre.pyi
+++ b/stdlib/@python2/_sre.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Dict, Iterable, List, Mapping, Optional, Sequence, Tuple, Union, overload
+from typing import Any, Dict, Iterable, List, Mapping, Sequence, Tuple, overload
 
 CODESIZE: int
 MAGIC: int
@@ -12,9 +12,9 @@ class SRE_Match(object):
     @overload
     def group(self) -> str: ...
     @overload
-    def group(self, group: int = ...) -> Optional[str]: ...
-    def groupdict(self) -> Dict[int, Optional[str]]: ...
-    def groups(self) -> Tuple[Optional[str], ...]: ...
+    def group(self, group: int = ...) -> str | None: ...
+    def groupdict(self) -> Dict[int, str | None]: ...
+    def groups(self) -> Tuple[str | None, ...]: ...
     def span(self) -> Tuple[int, int]: ...
     @property
     def regs(self) -> Tuple[Tuple[int, int], ...]: ...  # undocumented
@@ -30,12 +30,12 @@ class SRE_Pattern(object):
     groups: int
     groupindex: Mapping[str, int]
     indexgroup: Sequence[int]
-    def findall(self, source: str, pos: int = ..., endpos: int = ...) -> List[Union[Tuple[Any, ...], str]]: ...
-    def finditer(self, source: str, pos: int = ..., endpos: int = ...) -> Iterable[Union[Tuple[Any, ...], str]]: ...
+    def findall(self, source: str, pos: int = ..., endpos: int = ...) -> List[Tuple[Any, ...] | str]: ...
+    def finditer(self, source: str, pos: int = ..., endpos: int = ...) -> Iterable[Tuple[Any, ...] | str]: ...
     def match(self, pattern, pos: int = ..., endpos: int = ...) -> SRE_Match: ...
     def scanner(self, s: str, start: int = ..., end: int = ...) -> SRE_Scanner: ...
     def search(self, pattern, pos: int = ..., endpos: int = ...) -> SRE_Match: ...
-    def split(self, source: str, maxsplit: int = ...) -> List[Optional[str]]: ...
+    def split(self, source: str, maxsplit: int = ...) -> List[str | None]: ...
     def sub(self, repl: str, string: str, count: int = ...) -> Tuple[Any, ...]: ...
     def subn(self, repl: str, string: str, count: int = ...) -> Tuple[Any, ...]: ...
 
diff --git a/stdlib/@python2/_thread.pyi b/stdlib/@python2/_thread.pyi
index 46a6c7741024..562ece61e042 100644
--- a/stdlib/@python2/_thread.pyi
+++ b/stdlib/@python2/_thread.pyi
@@ -1,5 +1,5 @@
 from types import TracebackType
-from typing import Any, Callable, Dict, NoReturn, Optional, Tuple, Type
+from typing import Any, Callable, Dict, NoReturn, Tuple, Type
 
 error = RuntimeError
 
@@ -13,7 +13,7 @@ class LockType:
     def locked(self) -> bool: ...
     def __enter__(self) -> bool: ...
     def __exit__(
-        self, type: Optional[Type[BaseException]], value: Optional[BaseException], traceback: Optional[TracebackType]
+        self, type: Type[BaseException] | None, value: BaseException | None, traceback: TracebackType | None
     ) -> None: ...
 
 def start_new_thread(function: Callable[..., Any], args: Tuple[Any, ...], kwargs: Dict[str, Any] = ...) -> int: ...
diff --git a/stdlib/@python2/_typeshed/wsgi.pyi b/stdlib/@python2/_typeshed/wsgi.pyi
index bafaf7bc5f66..a1f10443a6f0 100644
--- a/stdlib/@python2/_typeshed/wsgi.pyi
+++ b/stdlib/@python2/_typeshed/wsgi.pyi
@@ -8,7 +8,7 @@ from typing import Any, Callable, Dict, Iterable, List, Optional, Protocol, Text
 
 class StartResponse(Protocol):
     def __call__(
-        self, status: str, headers: List[Tuple[str, str]], exc_info: Optional[_OptExcInfo] = ...
+        self, status: str, headers: List[Tuple[str, str]], exc_info: _OptExcInfo | None = ...
     ) -> Callable[[bytes], Any]: ...
 
 WSGIEnvironment = Dict[Text, Any]
diff --git a/stdlib/@python2/_typeshed/xml.pyi b/stdlib/@python2/_typeshed/xml.pyi
index 7ad28aef1b75..6a5d2531ca72 100644
--- a/stdlib/@python2/_typeshed/xml.pyi
+++ b/stdlib/@python2/_typeshed/xml.pyi
@@ -1,10 +1,10 @@
 # Stub-only types. This module does not exist at runtime.
 
-from typing import Any, Optional
+from typing import Any
 from typing_extensions import Protocol
 
 # As defined https://docs.python.org/3/library/xml.dom.html#domimplementation-objects
 class DOMImplementation(Protocol):
-    def hasFeature(self, feature: str, version: Optional[str]) -> bool: ...
-    def createDocument(self, namespaceUri: str, qualifiedName: str, doctype: Optional[Any]) -> Any: ...
+    def hasFeature(self, feature: str, version: str | None) -> bool: ...
+    def createDocument(self, namespaceUri: str, qualifiedName: str, doctype: Any | None) -> Any: ...
     def createDocumentType(self, qualifiedName: str, publicId: str, systemId: str) -> Any: ...
diff --git a/stdlib/@python2/_warnings.pyi b/stdlib/@python2/_warnings.pyi
index d16637e6814c..ccc51fecb8da 100644
--- a/stdlib/@python2/_warnings.pyi
+++ b/stdlib/@python2/_warnings.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Dict, List, Optional, Tuple, Type, Union, overload
+from typing import Any, Dict, List, Tuple, Type, overload
 
 default_action: str
 once_registry: Dict[Any, Any]
@@ -6,7 +6,7 @@ once_registry: Dict[Any, Any]
 filters: List[Tuple[Any, ...]]
 
 @overload
-def warn(message: str, category: Optional[Type[Warning]] = ..., stacklevel: int = ...) -> None: ...
+def warn(message: str, category: Type[Warning] | None = ..., stacklevel: int = ...) -> None: ...
 @overload
 def warn(message: Warning, category: Any = ..., stacklevel: int = ...) -> None: ...
 @overload
@@ -15,9 +15,9 @@ def warn_explicit(
     category: Type[Warning],
     filename: str,
     lineno: int,
-    module: Optional[str] = ...,
-    registry: Optional[Dict[Union[str, Tuple[str, Type[Warning], int]], int]] = ...,
-    module_globals: Optional[Dict[str, Any]] = ...,
+    module: str | None = ...,
+    registry: Dict[str | Tuple[str, Type[Warning], int], int] | None = ...,
+    module_globals: Dict[str, Any] | None = ...,
 ) -> None: ...
 @overload
 def warn_explicit(
@@ -25,7 +25,7 @@ def warn_explicit(
     category: Any,
     filename: str,
     lineno: int,
-    module: Optional[str] = ...,
-    registry: Optional[Dict[Union[str, Tuple[str, Type[Warning], int]], int]] = ...,
-    module_globals: Optional[Dict[str, Any]] = ...,
+    module: str | None = ...,
+    registry: Dict[str | Tuple[str, Type[Warning], int], int] | None = ...,
+    module_globals: Dict[str, Any] | None = ...,
 ) -> None: ...
diff --git a/stdlib/@python2/_weakref.pyi b/stdlib/@python2/_weakref.pyi
index e8882b6f18b8..a283d4cb60d3 100644
--- a/stdlib/@python2/_weakref.pyi
+++ b/stdlib/@python2/_weakref.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, Generic, List, Optional, TypeVar, overload
+from typing import Any, Callable, Generic, List, TypeVar, overload
 
 _C = TypeVar("_C", bound=Callable[..., Any])
 _T = TypeVar("_T")
@@ -10,8 +10,8 @@ class ProxyType(Generic[_T]):  # "weakproxy"
     def __getattr__(self, attr: str) -> Any: ...
 
 class ReferenceType(Generic[_T]):
-    def __init__(self, o: _T, callback: Optional[Callable[[ReferenceType[_T]], Any]] = ...) -> None: ...
-    def __call__(self) -> Optional[_T]: ...
+    def __init__(self, o: _T, callback: Callable[[ReferenceType[_T]], Any] | None = ...) -> None: ...
+    def __call__(self) -> _T | None: ...
     def __hash__(self) -> int: ...
 
 ref = ReferenceType
@@ -19,8 +19,8 @@ ref = ReferenceType
 def getweakrefcount(__object: Any) -> int: ...
 def getweakrefs(object: Any) -> List[Any]: ...
 @overload
-def proxy(object: _C, callback: Optional[Callable[[_C], Any]] = ...) -> CallableProxyType[_C]: ...
+def proxy(object: _C, callback: Callable[[_C], Any] | None = ...) -> CallableProxyType[_C]: ...
 
 # Return CallableProxyType if object is callable, ProxyType otherwise
 @overload
-def proxy(object: _T, callback: Optional[Callable[[_T], Any]] = ...) -> Any: ...
+def proxy(object: _T, callback: Callable[[_T], Any] | None = ...) -> Any: ...
diff --git a/stdlib/@python2/_weakrefset.pyi b/stdlib/@python2/_weakrefset.pyi
index 99fa3e31166a..f2cde7d67e52 100644
--- a/stdlib/@python2/_weakrefset.pyi
+++ b/stdlib/@python2/_weakrefset.pyi
@@ -1,11 +1,11 @@
-from typing import Any, Generic, Iterable, Iterator, MutableSet, Optional, TypeVar, Union
+from typing import Any, Generic, Iterable, Iterator, MutableSet, TypeVar
 
 _S = TypeVar("_S")
 _T = TypeVar("_T")
 _SelfT = TypeVar("_SelfT", bound=WeakSet[Any])
 
 class WeakSet(MutableSet[_T], Generic[_T]):
-    def __init__(self, data: Optional[Iterable[_T]] = ...) -> None: ...
+    def __init__(self, data: Iterable[_T] | None = ...) -> None: ...
     def add(self, item: _T) -> None: ...
     def clear(self) -> None: ...
     def discard(self, item: _T) -> None: ...
@@ -16,7 +16,7 @@ class WeakSet(MutableSet[_T], Generic[_T]):
     def __contains__(self, item: object) -> bool: ...
     def __len__(self) -> int: ...
     def __iter__(self) -> Iterator[_T]: ...
-    def __ior__(self, other: Iterable[_S]) -> WeakSet[Union[_S, _T]]: ...
+    def __ior__(self, other: Iterable[_S]) -> WeakSet[_S | _T]: ...
     def difference(self: _SelfT, other: Iterable[_T]) -> _SelfT: ...
     def __sub__(self: _SelfT, other: Iterable[_T]) -> _SelfT: ...
     def difference_update(self, other: Iterable[_T]) -> None: ...
@@ -32,10 +32,10 @@ class WeakSet(MutableSet[_T], Generic[_T]):
     def __ge__(self, other: Iterable[_T]) -> bool: ...
     def __gt__(self, other: Iterable[_T]) -> bool: ...
     def __eq__(self, other: object) -> bool: ...
-    def symmetric_difference(self, other: Iterable[_S]) -> WeakSet[Union[_S, _T]]: ...
-    def __xor__(self, other: Iterable[_S]) -> WeakSet[Union[_S, _T]]: ...
+    def symmetric_difference(self, other: Iterable[_S]) -> WeakSet[_S | _T]: ...
+    def __xor__(self, other: Iterable[_S]) -> WeakSet[_S | _T]: ...
     def symmetric_difference_update(self, other: Iterable[Any]) -> None: ...
-    def __ixor__(self, other: Iterable[_S]) -> WeakSet[Union[_S, _T]]: ...
-    def union(self, other: Iterable[_S]) -> WeakSet[Union[_S, _T]]: ...
-    def __or__(self, other: Iterable[_S]) -> WeakSet[Union[_S, _T]]: ...
+    def __ixor__(self, other: Iterable[_S]) -> WeakSet[_S | _T]: ...
+    def union(self, other: Iterable[_S]) -> WeakSet[_S | _T]: ...
+    def __or__(self, other: Iterable[_S]) -> WeakSet[_S | _T]: ...
     def isdisjoint(self, other: Iterable[_T]) -> bool: ...
diff --git a/stdlib/@python2/_winreg.pyi b/stdlib/@python2/_winreg.pyi
index 8e729f68720e..7297626ac8b3 100644
--- a/stdlib/@python2/_winreg.pyi
+++ b/stdlib/@python2/_winreg.pyi
@@ -1,12 +1,12 @@
 from types import TracebackType
-from typing import Any, Optional, Tuple, Type, Union
+from typing import Any, Tuple, Type, Union
 
 _KeyType = Union[HKEYType, int]
 
 def CloseKey(__hkey: _KeyType) -> None: ...
-def ConnectRegistry(__computer_name: Optional[str], __key: _KeyType) -> HKEYType: ...
-def CreateKey(__key: _KeyType, __sub_key: Optional[str]) -> HKEYType: ...
-def CreateKeyEx(key: _KeyType, sub_key: Optional[str], reserved: int = ..., access: int = ...) -> HKEYType: ...
+def ConnectRegistry(__computer_name: str | None, __key: _KeyType) -> HKEYType: ...
+def CreateKey(__key: _KeyType, __sub_key: str | None) -> HKEYType: ...
+def CreateKeyEx(key: _KeyType, sub_key: str | None, reserved: int = ..., access: int = ...) -> HKEYType: ...
 def DeleteKey(__key: _KeyType, __sub_key: str) -> None: ...
 def DeleteKeyEx(key: _KeyType, sub_key: str, access: int = ..., reserved: int = ...) -> None: ...
 def DeleteValue(__key: _KeyType, __value: str) -> None: ...
@@ -18,12 +18,12 @@ def LoadKey(__key: _KeyType, __sub_key: str, __file_name: str) -> None: ...
 def OpenKey(key: _KeyType, sub_key: str, reserved: int = ..., access: int = ...) -> HKEYType: ...
 def OpenKeyEx(key: _KeyType, sub_key: str, reserved: int = ..., access: int = ...) -> HKEYType: ...
 def QueryInfoKey(__key: _KeyType) -> Tuple[int, int, int]: ...
-def QueryValue(__key: _KeyType, __sub_key: Optional[str]) -> str: ...
+def QueryValue(__key: _KeyType, __sub_key: str | None) -> str: ...
 def QueryValueEx(__key: _KeyType, __name: str) -> Tuple[Any, int]: ...
 def SaveKey(__key: _KeyType, __file_name: str) -> None: ...
 def SetValue(__key: _KeyType, __sub_key: str, __type: int, __value: str) -> None: ...
 def SetValueEx(
-    __key: _KeyType, __value_name: Optional[str], __reserved: Any, __type: int, __value: Union[str, int]
+    __key: _KeyType, __value_name: str | None, __reserved: Any, __type: int, __value: str | int
 ) -> None: ...  # reserved is ignored
 def DisableReflectionKey(__key: _KeyType) -> None: ...
 def EnableReflectionKey(__key: _KeyType) -> None: ...
@@ -90,7 +90,7 @@ class HKEYType:
     def __int__(self) -> int: ...
     def __enter__(self) -> HKEYType: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def Close(self) -> None: ...
     def Detach(self) -> int: ...
diff --git a/stdlib/@python2/aifc.pyi b/stdlib/@python2/aifc.pyi
index 4349b11c1f1c..42f20b7466a1 100644
--- a/stdlib/@python2/aifc.pyi
+++ b/stdlib/@python2/aifc.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, List, NamedTuple, Optional, Text, Tuple, Union, overload
+from typing import IO, Any, List, NamedTuple, Text, Tuple, Union, overload
 from typing_extensions import Literal
 
 class Error(Exception): ...
@@ -28,7 +28,7 @@ class Aifc_read:
     def getcomptype(self) -> bytes: ...
     def getcompname(self) -> bytes: ...
     def getparams(self) -> _aifc_params: ...
-    def getmarkers(self) -> Optional[List[_Marker]]: ...
+    def getmarkers(self) -> List[_Marker] | None: ...
     def getmark(self, id: int) -> _Marker: ...
     def setpos(self, pos: int) -> None: ...
     def readframes(self, nframes: int) -> bytes: ...
@@ -54,7 +54,7 @@ class Aifc_write:
     def getparams(self) -> _aifc_params: ...
     def setmark(self, id: int, pos: int, name: bytes) -> None: ...
     def getmark(self, id: int) -> _Marker: ...
-    def getmarkers(self) -> Optional[List[_Marker]]: ...
+    def getmarkers(self) -> List[_Marker] | None: ...
     def tell(self) -> int: ...
     def writeframesraw(self, data: Any) -> None: ...  # Actual type for data is Buffer Protocol
     def writeframes(self, data: Any) -> None: ...
@@ -65,10 +65,10 @@ def open(f: _File, mode: Literal["r", "rb"]) -> Aifc_read: ...
 @overload
 def open(f: _File, mode: Literal["w", "wb"]) -> Aifc_write: ...
 @overload
-def open(f: _File, mode: Optional[str] = ...) -> Any: ...
+def open(f: _File, mode: str | None = ...) -> Any: ...
 @overload
 def openfp(f: _File, mode: Literal["r", "rb"]) -> Aifc_read: ...
 @overload
 def openfp(f: _File, mode: Literal["w", "wb"]) -> Aifc_write: ...
 @overload
-def openfp(f: _File, mode: Optional[str] = ...) -> Any: ...
+def openfp(f: _File, mode: str | None = ...) -> Any: ...
diff --git a/stdlib/@python2/argparse.pyi b/stdlib/@python2/argparse.pyi
index a3b5528c4a31..4d77f6582c5f 100644
--- a/stdlib/@python2/argparse.pyi
+++ b/stdlib/@python2/argparse.pyi
@@ -7,7 +7,6 @@ from typing import (
     Iterable,
     List,
     NoReturn,
-    Optional,
     Pattern,
     Protocol,
     Sequence,
@@ -34,9 +33,9 @@ ZERO_OR_MORE: str
 _UNRECOGNIZED_ARGS_ATTR: str  # undocumented
 
 class ArgumentError(Exception):
-    argument_name: Optional[str]
+    argument_name: str | None
     message: str
-    def __init__(self, argument: Optional[Action], message: str) -> None: ...
+    def __init__(self, argument: Action | None, message: str) -> None: ...
 
 # undocumented
 class _AttributeHolder:
@@ -45,7 +44,7 @@ class _AttributeHolder:
 
 # undocumented
 class _ActionsContainer:
-    description: Optional[_Text]
+    description: _Text | None
     prefix_chars: _Text
     argument_default: Any
     conflict_handler: _Text
@@ -58,9 +57,7 @@ class _ActionsContainer:
     _defaults: Dict[str, Any]
     _negative_number_matcher: Pattern[str]
     _has_negative_number_optionals: List[bool]
-    def __init__(
-        self, description: Optional[Text], prefix_chars: Text, argument_default: Any, conflict_handler: Text
-    ) -> None: ...
+    def __init__(self, description: Text | None, prefix_chars: Text, argument_default: Any, conflict_handler: Text) -> None: ...
     def register(self, registry_name: Text, value: Any, object: Any) -> None: ...
     def _registry_get(self, registry_name: Text, value: Any, default: Any = ...) -> Any: ...
     def set_defaults(self, **kwargs: Any) -> None: ...
@@ -68,16 +65,16 @@ class _ActionsContainer:
     def add_argument(
         self,
         *name_or_flags: Text,
-        action: Union[Text, Type[Action]] = ...,
-        nargs: Union[int, Text] = ...,
+        action: Text | Type[Action] = ...,
+        nargs: int | Text = ...,
         const: Any = ...,
         default: Any = ...,
-        type: Union[Callable[[Text], _T], Callable[[str], _T], FileType] = ...,
+        type: Callable[[Text], _T] | Callable[[str], _T] | FileType = ...,
         choices: Iterable[_T] = ...,
         required: bool = ...,
-        help: Optional[Text] = ...,
-        metavar: Optional[Union[Text, Tuple[Text, ...]]] = ...,
-        dest: Optional[Text] = ...,
+        help: Text | None = ...,
+        metavar: Text | Tuple[Text, ...] | None = ...,
+        dest: Text | None = ...,
         version: Text = ...,
         **kwargs: Any,
     ) -> Action: ...
@@ -88,7 +85,7 @@ class _ActionsContainer:
     def _add_container_actions(self, container: _ActionsContainer) -> None: ...
     def _get_positional_kwargs(self, dest: Text, **kwargs: Any) -> Dict[str, Any]: ...
     def _get_optional_kwargs(self, *args: Any, **kwargs: Any) -> Dict[str, Any]: ...
-    def _pop_action_class(self, kwargs: Any, default: Optional[Type[Action]] = ...) -> Type[Action]: ...
+    def _pop_action_class(self, kwargs: Any, default: Type[Action] | None = ...) -> Type[Action]: ...
     def _get_handler(self) -> Callable[[Action, Iterable[Tuple[Text, Action]]], Any]: ...
     def _check_conflict(self, action: Action) -> None: ...
     def _handle_conflict_error(self, action: Action, conflicting_actions: Iterable[Tuple[Text, Action]]) -> NoReturn: ...
@@ -99,26 +96,26 @@ class _FormatterClass(Protocol):
 
 class ArgumentParser(_AttributeHolder, _ActionsContainer):
     prog: _Text
-    usage: Optional[_Text]
-    epilog: Optional[_Text]
+    usage: _Text | None
+    epilog: _Text | None
     formatter_class: _FormatterClass
-    fromfile_prefix_chars: Optional[_Text]
+    fromfile_prefix_chars: _Text | None
     add_help: bool
 
     # undocumented
     _positionals: _ArgumentGroup
     _optionals: _ArgumentGroup
-    _subparsers: Optional[_ArgumentGroup]
+    _subparsers: _ArgumentGroup | None
     def __init__(
         self,
-        prog: Optional[Text] = ...,
-        usage: Optional[Text] = ...,
-        description: Optional[Text] = ...,
-        epilog: Optional[Text] = ...,
+        prog: Text | None = ...,
+        usage: Text | None = ...,
+        description: Text | None = ...,
+        epilog: Text | None = ...,
         parents: Sequence[ArgumentParser] = ...,
         formatter_class: _FormatterClass = ...,
         prefix_chars: Text = ...,
-        fromfile_prefix_chars: Optional[Text] = ...,
+        fromfile_prefix_chars: Text | None = ...,
         argument_default: Any = ...,
         conflict_handler: Text = ...,
         add_help: bool = ...,
@@ -126,11 +123,11 @@ class ArgumentParser(_AttributeHolder, _ActionsContainer):
     # The type-ignores in these overloads should be temporary.  See:
     # https://github.com/python/typeshed/pull/2643#issuecomment-442280277
     @overload
-    def parse_args(self, args: Optional[Sequence[Text]] = ...) -> Namespace: ...
+    def parse_args(self, args: Sequence[Text] | None = ...) -> Namespace: ...
     @overload
-    def parse_args(self, args: Optional[Sequence[Text]], namespace: None) -> Namespace: ...  # type: ignore
+    def parse_args(self, args: Sequence[Text] | None, namespace: None) -> Namespace: ...  # type: ignore
     @overload
-    def parse_args(self, args: Optional[Sequence[Text]], namespace: _N) -> _N: ...
+    def parse_args(self, args: Sequence[Text] | None, namespace: _N) -> _N: ...
     @overload
     def parse_args(self, *, namespace: None) -> Namespace: ...  # type: ignore
     @overload
@@ -139,24 +136,24 @@ class ArgumentParser(_AttributeHolder, _ActionsContainer):
         self,
         *,
         title: Text = ...,
-        description: Optional[Text] = ...,
+        description: Text | None = ...,
         prog: Text = ...,
         parser_class: Type[ArgumentParser] = ...,
         action: Type[Action] = ...,
         option_string: Text = ...,
-        dest: Optional[Text] = ...,
-        help: Optional[Text] = ...,
-        metavar: Optional[Text] = ...,
+        dest: Text | None = ...,
+        help: Text | None = ...,
+        metavar: Text | None = ...,
     ) -> _SubParsersAction: ...
-    def print_usage(self, file: Optional[IO[str]] = ...) -> None: ...
-    def print_help(self, file: Optional[IO[str]] = ...) -> None: ...
+    def print_usage(self, file: IO[str] | None = ...) -> None: ...
+    def print_help(self, file: IO[str] | None = ...) -> None: ...
     def format_usage(self) -> str: ...
     def format_help(self) -> str: ...
     def parse_known_args(
-        self, args: Optional[Sequence[Text]] = ..., namespace: Optional[Namespace] = ...
+        self, args: Sequence[Text] | None = ..., namespace: Namespace | None = ...
     ) -> Tuple[Namespace, List[str]]: ...
     def convert_arg_line_to_args(self, arg_line: Text) -> List[str]: ...
-    def exit(self, status: int = ..., message: Optional[Text] = ...) -> NoReturn: ...
+    def exit(self, status: int = ..., message: Text | None = ...) -> NoReturn: ...
     def error(self, message: Text) -> NoReturn: ...
     # undocumented
     def _get_optional_actions(self) -> List[Action]: ...
@@ -165,14 +162,14 @@ class ArgumentParser(_AttributeHolder, _ActionsContainer):
     def _read_args_from_files(self, arg_strings: List[Text]) -> List[Text]: ...
     def _match_argument(self, action: Action, arg_strings_pattern: Text) -> int: ...
     def _match_arguments_partial(self, actions: Sequence[Action], arg_strings_pattern: Text) -> List[int]: ...
-    def _parse_optional(self, arg_string: Text) -> Optional[Tuple[Optional[Action], Text, Optional[Text]]]: ...
-    def _get_option_tuples(self, option_string: Text) -> List[Tuple[Action, Text, Optional[Text]]]: ...
+    def _parse_optional(self, arg_string: Text) -> Tuple[Action | None, Text, Text | None] | None: ...
+    def _get_option_tuples(self, option_string: Text) -> List[Tuple[Action, Text, Text | None]]: ...
     def _get_nargs_pattern(self, action: Action) -> _Text: ...
     def _get_values(self, action: Action, arg_strings: List[Text]) -> Any: ...
     def _get_value(self, action: Action, arg_string: Text) -> Any: ...
     def _check_value(self, action: Action, value: Any) -> None: ...
     def _get_formatter(self) -> HelpFormatter: ...
-    def _print_message(self, message: str, file: Optional[IO[str]] = ...) -> None: ...
+    def _print_message(self, message: str, file: IO[str] | None = ...) -> None: ...
 
 class HelpFormatter:
     # undocumented
@@ -189,23 +186,23 @@ class HelpFormatter:
     _long_break_matcher: Pattern[str]
     _Section: Type[Any]  # Nested class
     def __init__(
-        self, prog: Text, indent_increment: int = ..., max_help_position: int = ..., width: Optional[int] = ...
+        self, prog: Text, indent_increment: int = ..., max_help_position: int = ..., width: int | None = ...
     ) -> None: ...
     def _indent(self) -> None: ...
     def _dedent(self) -> None: ...
     def _add_item(self, func: Callable[..., _Text], args: Iterable[Any]) -> None: ...
-    def start_section(self, heading: Optional[Text]) -> None: ...
+    def start_section(self, heading: Text | None) -> None: ...
     def end_section(self) -> None: ...
-    def add_text(self, text: Optional[Text]) -> None: ...
+    def add_text(self, text: Text | None) -> None: ...
     def add_usage(
-        self, usage: Optional[Text], actions: Iterable[Action], groups: Iterable[_ArgumentGroup], prefix: Optional[Text] = ...
+        self, usage: Text | None, actions: Iterable[Action], groups: Iterable[_ArgumentGroup], prefix: Text | None = ...
     ) -> None: ...
     def add_argument(self, action: Action) -> None: ...
     def add_arguments(self, actions: Iterable[Action]) -> None: ...
     def format_help(self) -> _Text: ...
     def _join_parts(self, part_strings: Iterable[Text]) -> _Text: ...
     def _format_usage(
-        self, usage: Text, actions: Iterable[Action], groups: Iterable[_ArgumentGroup], prefix: Optional[Text]
+        self, usage: Text, actions: Iterable[Action], groups: Iterable[_ArgumentGroup], prefix: Text | None
     ) -> _Text: ...
     def _format_actions_usage(self, actions: Iterable[Action], groups: Iterable[_ArgumentGroup]) -> _Text: ...
     def _format_text(self, text: Text) -> _Text: ...
@@ -217,7 +214,7 @@ class HelpFormatter:
     def _iter_indented_subactions(self, action: Action) -> Generator[Action, None, None]: ...
     def _split_lines(self, text: Text, width: int) -> List[_Text]: ...
     def _fill_text(self, text: Text, width: int, indent: Text) -> _Text: ...
-    def _get_help_string(self, action: Action) -> Optional[_Text]: ...
+    def _get_help_string(self, action: Action) -> _Text | None: ...
     def _get_default_metavar_for_optional(self, action: Action) -> _Text: ...
     def _get_default_metavar_for_positional(self, action: Action) -> _Text: ...
 
@@ -228,33 +225,29 @@ class ArgumentDefaultsHelpFormatter(HelpFormatter): ...
 class Action(_AttributeHolder):
     option_strings: Sequence[_Text]
     dest: _Text
-    nargs: Optional[Union[int, _Text]]
+    nargs: int | _Text | None
     const: Any
     default: Any
-    type: Union[Callable[[str], Any], FileType, None]
-    choices: Optional[Iterable[Any]]
+    type: Callable[[str], Any] | FileType | None
+    choices: Iterable[Any] | None
     required: bool
-    help: Optional[_Text]
-    metavar: Optional[Union[_Text, Tuple[_Text, ...]]]
+    help: _Text | None
+    metavar: _Text | Tuple[_Text, ...] | None
     def __init__(
         self,
         option_strings: Sequence[Text],
         dest: Text,
-        nargs: Optional[Union[int, Text]] = ...,
-        const: Optional[_T] = ...,
-        default: Union[_T, str, None] = ...,
-        type: Optional[Union[Callable[[Text], _T], Callable[[str], _T], FileType]] = ...,
-        choices: Optional[Iterable[_T]] = ...,
+        nargs: int | Text | None = ...,
+        const: _T | None = ...,
+        default: _T | str | None = ...,
+        type: Callable[[Text], _T] | Callable[[str], _T] | FileType | None = ...,
+        choices: Iterable[_T] | None = ...,
         required: bool = ...,
-        help: Optional[Text] = ...,
-        metavar: Optional[Union[Text, Tuple[Text, ...]]] = ...,
+        help: Text | None = ...,
+        metavar: Text | Tuple[Text, ...] | None = ...,
     ) -> None: ...
     def __call__(
-        self,
-        parser: ArgumentParser,
-        namespace: Namespace,
-        values: Union[Text, Sequence[Any], None],
-        option_string: Optional[Text] = ...,
+        self, parser: ArgumentParser, namespace: Namespace, values: Text | Sequence[Any] | None, option_string: Text | None = ...
     ) -> None: ...
 
 class Namespace(_AttributeHolder):
@@ -267,15 +260,15 @@ class FileType:
     # undocumented
     _mode: _Text
     _bufsize: int
-    def __init__(self, mode: Text = ..., bufsize: Optional[int] = ...) -> None: ...
+    def __init__(self, mode: Text = ..., bufsize: int | None = ...) -> None: ...
     def __call__(self, string: Text) -> IO[Any]: ...
 
 # undocumented
 class _ArgumentGroup(_ActionsContainer):
-    title: Optional[_Text]
+    title: _Text | None
     _group_actions: List[Action]
     def __init__(
-        self, container: _ActionsContainer, title: Optional[Text] = ..., description: Optional[Text] = ..., **kwargs: Any
+        self, container: _ActionsContainer, title: Text | None = ..., description: Text | None = ..., **kwargs: Any
     ) -> None: ...
 
 # undocumented
@@ -296,20 +289,20 @@ class _StoreConstAction(Action):
         const: Any,
         default: Any = ...,
         required: bool = ...,
-        help: Optional[Text] = ...,
-        metavar: Optional[Union[Text, Tuple[Text, ...]]] = ...,
+        help: Text | None = ...,
+        metavar: Text | Tuple[Text, ...] | None = ...,
     ) -> None: ...
 
 # undocumented
 class _StoreTrueAction(_StoreConstAction):
     def __init__(
-        self, option_strings: Sequence[Text], dest: Text, default: bool = ..., required: bool = ..., help: Optional[Text] = ...
+        self, option_strings: Sequence[Text], dest: Text, default: bool = ..., required: bool = ..., help: Text | None = ...
     ) -> None: ...
 
 # undocumented
 class _StoreFalseAction(_StoreConstAction):
     def __init__(
-        self, option_strings: Sequence[Text], dest: Text, default: bool = ..., required: bool = ..., help: Optional[Text] = ...
+        self, option_strings: Sequence[Text], dest: Text, default: bool = ..., required: bool = ..., help: Text | None = ...
     ) -> None: ...
 
 # undocumented
@@ -324,32 +317,27 @@ class _AppendConstAction(Action):
         const: Any,
         default: Any = ...,
         required: bool = ...,
-        help: Optional[Text] = ...,
-        metavar: Optional[Union[Text, Tuple[Text, ...]]] = ...,
+        help: Text | None = ...,
+        metavar: Text | Tuple[Text, ...] | None = ...,
     ) -> None: ...
 
 # undocumented
 class _CountAction(Action):
     def __init__(
-        self, option_strings: Sequence[Text], dest: Text, default: Any = ..., required: bool = ..., help: Optional[Text] = ...
+        self, option_strings: Sequence[Text], dest: Text, default: Any = ..., required: bool = ..., help: Text | None = ...
     ) -> None: ...
 
 # undocumented
 class _HelpAction(Action):
     def __init__(
-        self, option_strings: Sequence[Text], dest: Text = ..., default: Text = ..., help: Optional[Text] = ...
+        self, option_strings: Sequence[Text], dest: Text = ..., default: Text = ..., help: Text | None = ...
     ) -> None: ...
 
 # undocumented
 class _VersionAction(Action):
-    version: Optional[_Text]
+    version: _Text | None
     def __init__(
-        self,
-        option_strings: Sequence[Text],
-        version: Optional[Text] = ...,
-        dest: Text = ...,
-        default: Text = ...,
-        help: Text = ...,
+        self, option_strings: Sequence[Text], version: Text | None = ..., dest: Text = ..., default: Text = ..., help: Text = ...
     ) -> None: ...
 
 # undocumented
@@ -366,8 +354,8 @@ class _SubParsersAction(Action):
         prog: Text,
         parser_class: Type[ArgumentParser],
         dest: Text = ...,
-        help: Optional[Text] = ...,
-        metavar: Optional[Union[Text, Tuple[Text, ...]]] = ...,
+        help: Text | None = ...,
+        metavar: Text | Tuple[Text, ...] | None = ...,
     ) -> None: ...
     # TODO: Type keyword args properly.
     def add_parser(self, name: Text, **kwargs: Any) -> ArgumentParser: ...
@@ -380,4 +368,4 @@ class ArgumentTypeError(Exception): ...
 def _ensure_value(namespace: Namespace, name: Text, value: Any) -> Any: ...
 
 # undocumented
-def _get_action_name(argument: Optional[Action]) -> Optional[str]: ...
+def _get_action_name(argument: Action | None) -> str | None: ...
diff --git a/stdlib/@python2/array.pyi b/stdlib/@python2/array.pyi
index a93742f85412..39670fe734fc 100644
--- a/stdlib/@python2/array.pyi
+++ b/stdlib/@python2/array.pyi
@@ -12,13 +12,13 @@ class array(MutableSequence[_T], Generic[_T]):
     typecode: _TypeCode
     itemsize: int
     @overload
-    def __init__(self: array[int], typecode: _IntTypeCode, __initializer: Union[bytes, Iterable[_T]] = ...) -> None: ...
+    def __init__(self: array[int], typecode: _IntTypeCode, __initializer: bytes | Iterable[_T] = ...) -> None: ...
     @overload
-    def __init__(self: array[float], typecode: _FloatTypeCode, __initializer: Union[bytes, Iterable[_T]] = ...) -> None: ...
+    def __init__(self: array[float], typecode: _FloatTypeCode, __initializer: bytes | Iterable[_T] = ...) -> None: ...
     @overload
-    def __init__(self: array[Text], typecode: _UnicodeTypeCode, __initializer: Union[bytes, Iterable[_T]] = ...) -> None: ...
+    def __init__(self: array[Text], typecode: _UnicodeTypeCode, __initializer: bytes | Iterable[_T] = ...) -> None: ...
     @overload
-    def __init__(self, typecode: str, __initializer: Union[bytes, Iterable[_T]] = ...) -> None: ...
+    def __init__(self, typecode: str, __initializer: bytes | Iterable[_T] = ...) -> None: ...
     def append(self, __v: _T) -> None: ...
     def buffer_info(self) -> Tuple[int, int]: ...
     def byteswap(self) -> None: ...
@@ -48,7 +48,7 @@ class array(MutableSequence[_T], Generic[_T]):
     def __setitem__(self, i: int, o: _T) -> None: ...
     @overload
     def __setitem__(self, s: slice, o: array[_T]) -> None: ...
-    def __delitem__(self, i: Union[int, slice]) -> None: ...
+    def __delitem__(self, i: int | slice) -> None: ...
     def __add__(self, x: array[_T]) -> array[_T]: ...
     def __ge__(self, other: array[_T]) -> bool: ...
     def __gt__(self, other: array[_T]) -> bool: ...
diff --git a/stdlib/@python2/ast.pyi b/stdlib/@python2/ast.pyi
index a8432dd85978..ec370e1a6c08 100644
--- a/stdlib/@python2/ast.pyi
+++ b/stdlib/@python2/ast.pyi
@@ -4,12 +4,12 @@
 # from _ast below when loaded in an unorthodox way by the Dropbox
 # internal Bazel integration.
 import typing as _typing
-from typing import Any, Iterator, Optional, Union
+from typing import Any, Iterator
 
 from _ast import *
 from _ast import AST, Module
 
-def parse(source: Union[str, unicode], filename: Union[str, unicode] = ..., mode: Union[str, unicode] = ...) -> Module: ...
+def parse(source: str | unicode, filename: str | unicode = ..., mode: str | unicode = ...) -> Module: ...
 def copy_location(new_node: AST, old_node: AST) -> AST: ...
 def dump(node: AST, annotate_fields: bool = ..., include_attributes: bool = ...) -> str: ...
 def fix_missing_locations(node: AST) -> AST: ...
@@ -17,7 +17,7 @@ def get_docstring(node: AST, clean: bool = ...) -> str: ...
 def increment_lineno(node: AST, n: int = ...) -> AST: ...
 def iter_child_nodes(node: AST) -> Iterator[AST]: ...
 def iter_fields(node: AST) -> Iterator[_typing.Tuple[str, Any]]: ...
-def literal_eval(node_or_string: Union[str, unicode, AST]) -> Any: ...
+def literal_eval(node_or_string: str | unicode | AST) -> Any: ...
 def walk(node: AST) -> Iterator[AST]: ...
 
 class NodeVisitor:
@@ -25,4 +25,4 @@ class NodeVisitor:
     def generic_visit(self, node: AST) -> Any: ...
 
 class NodeTransformer(NodeVisitor):
-    def generic_visit(self, node: AST) -> Optional[AST]: ...
+    def generic_visit(self, node: AST) -> AST | None: ...
diff --git a/stdlib/@python2/asynchat.pyi b/stdlib/@python2/asynchat.pyi
index 464eb42bad52..0f5526d71b1d 100644
--- a/stdlib/@python2/asynchat.pyi
+++ b/stdlib/@python2/asynchat.pyi
@@ -1,7 +1,7 @@
 import asyncore
 import socket
 from abc import abstractmethod
-from typing import Optional, Sequence, Tuple, Union
+from typing import Sequence, Tuple
 
 class simple_producer:
     def __init__(self, data: bytes, buffer_size: int = ...) -> None: ...
@@ -10,13 +10,13 @@ class simple_producer:
 class async_chat(asyncore.dispatcher):
     ac_in_buffer_size: int
     ac_out_buffer_size: int
-    def __init__(self, sock: Optional[socket.socket] = ..., map: Optional[asyncore._maptype] = ...) -> None: ...
+    def __init__(self, sock: socket.socket | None = ..., map: asyncore._maptype | None = ...) -> None: ...
     @abstractmethod
     def collect_incoming_data(self, data: bytes) -> None: ...
     @abstractmethod
     def found_terminator(self) -> None: ...
-    def set_terminator(self, term: Union[bytes, int, None]) -> None: ...
-    def get_terminator(self) -> Union[bytes, int, None]: ...
+    def set_terminator(self, term: bytes | int | None) -> None: ...
+    def get_terminator(self) -> bytes | int | None: ...
     def handle_read(self) -> None: ...
     def handle_write(self) -> None: ...
     def handle_close(self) -> None: ...
@@ -29,9 +29,9 @@ class async_chat(asyncore.dispatcher):
     def discard_buffers(self) -> None: ...
 
 class fifo:
-    def __init__(self, list: Sequence[Union[bytes, simple_producer]] = ...) -> None: ...
+    def __init__(self, list: Sequence[bytes | simple_producer] = ...) -> None: ...
     def __len__(self) -> int: ...
     def is_empty(self) -> bool: ...
     def first(self) -> bytes: ...
-    def push(self, data: Union[bytes, simple_producer]) -> None: ...
+    def push(self, data: bytes | simple_producer) -> None: ...
     def pop(self) -> Tuple[int, bytes]: ...
diff --git a/stdlib/@python2/asyncore.pyi b/stdlib/@python2/asyncore.pyi
index 5183e3471e85..95acf9b706d3 100644
--- a/stdlib/@python2/asyncore.pyi
+++ b/stdlib/@python2/asyncore.pyi
@@ -1,7 +1,7 @@
 import sys
 from _typeshed import FileDescriptorLike
 from socket import SocketType
-from typing import Any, Dict, Optional, Tuple, Union, overload
+from typing import Any, Dict, Optional, Tuple, overload
 
 # cyclic dependence with asynchat
 _maptype = Dict[int, Any]
@@ -13,12 +13,12 @@ class ExitNow(Exception): ...
 def read(obj: Any) -> None: ...
 def write(obj: Any) -> None: ...
 def readwrite(obj: Any, flags: int) -> None: ...
-def poll(timeout: float = ..., map: Optional[_maptype] = ...) -> None: ...
-def poll2(timeout: float = ..., map: Optional[_maptype] = ...) -> None: ...
+def poll(timeout: float = ..., map: _maptype | None = ...) -> None: ...
+def poll2(timeout: float = ..., map: _maptype | None = ...) -> None: ...
 
 poll3 = poll2
 
-def loop(timeout: float = ..., use_poll: bool = ..., map: Optional[_maptype] = ..., count: Optional[int] = ...) -> None: ...
+def loop(timeout: float = ..., use_poll: bool = ..., map: _maptype | None = ..., count: int | None = ...) -> None: ...
 
 # Not really subclass of socket.socket; it's only delegation.
 # It is not covariant to it.
@@ -30,19 +30,19 @@ class dispatcher:
     connecting: bool
     closing: bool
     ignore_log_types: frozenset[str]
-    socket: Optional[SocketType]
-    def __init__(self, sock: Optional[SocketType] = ..., map: Optional[_maptype] = ...) -> None: ...
-    def add_channel(self, map: Optional[_maptype] = ...) -> None: ...
-    def del_channel(self, map: Optional[_maptype] = ...) -> None: ...
+    socket: SocketType | None
+    def __init__(self, sock: SocketType | None = ..., map: _maptype | None = ...) -> None: ...
+    def add_channel(self, map: _maptype | None = ...) -> None: ...
+    def del_channel(self, map: _maptype | None = ...) -> None: ...
     def create_socket(self, family: int = ..., type: int = ...) -> None: ...
-    def set_socket(self, sock: SocketType, map: Optional[_maptype] = ...) -> None: ...
+    def set_socket(self, sock: SocketType, map: _maptype | None = ...) -> None: ...
     def set_reuse_addr(self) -> None: ...
     def readable(self) -> bool: ...
     def writable(self) -> bool: ...
     def listen(self, num: int) -> None: ...
-    def bind(self, addr: Union[Tuple[Any, ...], str]) -> None: ...
-    def connect(self, address: Union[Tuple[Any, ...], str]) -> None: ...
-    def accept(self) -> Optional[Tuple[SocketType, Any]]: ...
+    def bind(self, addr: Tuple[Any, ...] | str) -> None: ...
+    def connect(self, address: Tuple[Any, ...] | str) -> None: ...
+    def accept(self) -> Tuple[SocketType, Any] | None: ...
     def send(self, data: bytes) -> int: ...
     def recv(self, buffer_size: int) -> bytes: ...
     def close(self) -> None: ...
@@ -83,21 +83,21 @@ class dispatcher:
     def recvfrom_into(self, buffer: bytes, nbytes: int, flags: int = ...) -> Any: ...
     def recv_into(self, buffer: bytes, nbytes: int, flags: int = ...) -> Any: ...
     def sendall(self, data: bytes, flags: int = ...) -> None: ...
-    def sendto(self, data: bytes, address: Union[Tuple[str, int], str], flags: int = ...) -> int: ...
+    def sendto(self, data: bytes, address: Tuple[str, int] | str, flags: int = ...) -> int: ...
     def setblocking(self, flag: bool) -> None: ...
-    def settimeout(self, value: Union[float, None]) -> None: ...
-    def setsockopt(self, level: int, optname: int, value: Union[int, bytes]) -> None: ...
+    def settimeout(self, value: float | None) -> None: ...
+    def setsockopt(self, level: int, optname: int, value: int | bytes) -> None: ...
     def shutdown(self, how: int) -> None: ...
 
 class dispatcher_with_send(dispatcher):
-    def __init__(self, sock: SocketType = ..., map: Optional[_maptype] = ...) -> None: ...
+    def __init__(self, sock: SocketType = ..., map: _maptype | None = ...) -> None: ...
     def initiate_send(self) -> None: ...
     def handle_write(self) -> None: ...
     # incompatible signature:
     # def send(self, data: bytes) -> Optional[int]: ...
 
 def compact_traceback() -> Tuple[Tuple[str, str, str], type, type, str]: ...
-def close_all(map: Optional[_maptype] = ..., ignore_all: bool = ...) -> None: ...
+def close_all(map: _maptype | None = ..., ignore_all: bool = ...) -> None: ...
 
 if sys.platform != "win32":
     class file_wrapper:
@@ -114,5 +114,5 @@ if sys.platform != "win32":
         def close(self) -> None: ...
         def fileno(self) -> int: ...
     class file_dispatcher(dispatcher):
-        def __init__(self, fd: FileDescriptorLike, map: Optional[_maptype] = ...) -> None: ...
+        def __init__(self, fd: FileDescriptorLike, map: _maptype | None = ...) -> None: ...
         def set_file(self, fd: int) -> None: ...
diff --git a/stdlib/@python2/audioop.pyi b/stdlib/@python2/audioop.pyi
index 606f4b9f5f7e..71671afe487e 100644
--- a/stdlib/@python2/audioop.pyi
+++ b/stdlib/@python2/audioop.pyi
@@ -1,4 +1,4 @@
-from typing import Optional, Tuple
+from typing import Tuple
 
 AdpcmState = Tuple[int, int]
 RatecvState = Tuple[int, Tuple[Tuple[int, int], ...]]
@@ -6,7 +6,7 @@ RatecvState = Tuple[int, Tuple[Tuple[int, int], ...]]
 class error(Exception): ...
 
 def add(__fragment1: bytes, __fragment2: bytes, __width: int) -> bytes: ...
-def adpcm2lin(__fragment: bytes, __width: int, __state: Optional[AdpcmState]) -> Tuple[bytes, AdpcmState]: ...
+def adpcm2lin(__fragment: bytes, __width: int, __state: AdpcmState | None) -> Tuple[bytes, AdpcmState]: ...
 def alaw2lin(__fragment: bytes, __width: int) -> bytes: ...
 def avg(__fragment: bytes, __width: int) -> int: ...
 def avgpp(__fragment: bytes, __width: int) -> int: ...
@@ -17,7 +17,7 @@ def findfactor(__fragment: bytes, __reference: bytes) -> float: ...
 def findfit(__fragment: bytes, __reference: bytes) -> Tuple[int, float]: ...
 def findmax(__fragment: bytes, __length: int) -> int: ...
 def getsample(__fragment: bytes, __width: int, __index: int) -> int: ...
-def lin2adpcm(__fragment: bytes, __width: int, __state: Optional[AdpcmState]) -> Tuple[bytes, AdpcmState]: ...
+def lin2adpcm(__fragment: bytes, __width: int, __state: AdpcmState | None) -> Tuple[bytes, AdpcmState]: ...
 def lin2alaw(__fragment: bytes, __width: int) -> bytes: ...
 def lin2lin(__fragment: bytes, __width: int, __newwidth: int) -> bytes: ...
 def lin2ulaw(__fragment: bytes, __width: int) -> bytes: ...
@@ -31,7 +31,7 @@ def ratecv(
     __nchannels: int,
     __inrate: int,
     __outrate: int,
-    __state: Optional[RatecvState],
+    __state: RatecvState | None,
     __weightA: int = ...,
     __weightB: int = ...,
 ) -> Tuple[bytes, RatecvState]: ...
diff --git a/stdlib/@python2/base64.pyi b/stdlib/@python2/base64.pyi
index 05c3ec319f38..00856aafddbe 100644
--- a/stdlib/@python2/base64.pyi
+++ b/stdlib/@python2/base64.pyi
@@ -1,16 +1,16 @@
-from typing import IO, Optional, Union
+from typing import IO, Union
 
 _encodable = Union[bytes, unicode]
 _decodable = Union[bytes, unicode]
 
-def b64encode(s: _encodable, altchars: Optional[bytes] = ...) -> bytes: ...
-def b64decode(s: _decodable, altchars: Optional[bytes] = ..., validate: bool = ...) -> bytes: ...
+def b64encode(s: _encodable, altchars: bytes | None = ...) -> bytes: ...
+def b64decode(s: _decodable, altchars: bytes | None = ..., validate: bool = ...) -> bytes: ...
 def standard_b64encode(s: _encodable) -> bytes: ...
 def standard_b64decode(s: _decodable) -> bytes: ...
 def urlsafe_b64encode(s: _encodable) -> bytes: ...
 def urlsafe_b64decode(s: _decodable) -> bytes: ...
 def b32encode(s: _encodable) -> bytes: ...
-def b32decode(s: _decodable, casefold: bool = ..., map01: Optional[bytes] = ...) -> bytes: ...
+def b32decode(s: _decodable, casefold: bool = ..., map01: bytes | None = ...) -> bytes: ...
 def b16encode(s: _encodable) -> bytes: ...
 def b16decode(s: _decodable, casefold: bool = ...) -> bytes: ...
 def decode(input: IO[bytes], output: IO[bytes]) -> None: ...
diff --git a/stdlib/@python2/bdb.pyi b/stdlib/@python2/bdb.pyi
index 9d76b3afde22..5bee9dadb928 100644
--- a/stdlib/@python2/bdb.pyi
+++ b/stdlib/@python2/bdb.pyi
@@ -1,5 +1,5 @@
 from types import CodeType, FrameType, TracebackType
-from typing import IO, Any, Callable, Dict, Iterable, List, Mapping, Optional, Set, SupportsInt, Tuple, Type, TypeVar, Union
+from typing import IO, Any, Callable, Dict, Iterable, List, Mapping, Set, SupportsInt, Tuple, Type, TypeVar
 
 _T = TypeVar("_T")
 _TraceDispatch = Callable[[FrameType, str, Any], Any]  # TODO: Recursive type
@@ -11,16 +11,16 @@ class BdbQuit(Exception): ...
 
 class Bdb:
 
-    skip: Optional[Set[str]]
+    skip: Set[str] | None
     breaks: Dict[str, List[int]]
     fncache: Dict[str, str]
-    frame_returning: Optional[FrameType]
-    botframe: Optional[FrameType]
+    frame_returning: FrameType | None
+    botframe: FrameType | None
     quitting: bool
-    stopframe: Optional[FrameType]
-    returnframe: Optional[FrameType]
+    stopframe: FrameType | None
+    returnframe: FrameType | None
     stoplineno: int
-    def __init__(self, skip: Optional[Iterable[str]] = ...) -> None: ...
+    def __init__(self, skip: Iterable[str] | None = ...) -> None: ...
     def canonic(self, filename: str) -> str: ...
     def reset(self) -> None: ...
     def trace_dispatch(self, frame: FrameType, event: str, arg: Any) -> _TraceDispatch: ...
@@ -31,21 +31,21 @@ class Bdb:
     def is_skipped_module(self, module_name: str) -> bool: ...
     def stop_here(self, frame: FrameType) -> bool: ...
     def break_here(self, frame: FrameType) -> bool: ...
-    def do_clear(self, arg: Any) -> Optional[bool]: ...
+    def do_clear(self, arg: Any) -> bool | None: ...
     def break_anywhere(self, frame: FrameType) -> bool: ...
     def user_call(self, frame: FrameType, argument_list: None) -> None: ...
     def user_line(self, frame: FrameType) -> None: ...
     def user_return(self, frame: FrameType, return_value: Any) -> None: ...
     def user_exception(self, frame: FrameType, exc_info: _ExcInfo) -> None: ...
-    def set_until(self, frame: FrameType, lineno: Optional[int] = ...) -> None: ...
+    def set_until(self, frame: FrameType, lineno: int | None = ...) -> None: ...
     def set_step(self) -> None: ...
     def set_next(self, frame: FrameType) -> None: ...
     def set_return(self, frame: FrameType) -> None: ...
-    def set_trace(self, frame: Optional[FrameType] = ...) -> None: ...
+    def set_trace(self, frame: FrameType | None = ...) -> None: ...
     def set_continue(self) -> None: ...
     def set_quit(self) -> None: ...
     def set_break(
-        self, filename: str, lineno: int, temporary: bool = ..., cond: Optional[str] = ..., funcname: Optional[str] = ...
+        self, filename: str, lineno: int, temporary: bool = ..., cond: str | None = ..., funcname: str | None = ...
     ) -> None: ...
     def clear_break(self, filename: str, lineno: int) -> None: ...
     def clear_bpbynumber(self, arg: SupportsInt) -> None: ...
@@ -56,43 +56,39 @@ class Bdb:
     def get_breaks(self, filename: str, lineno: int) -> List[Breakpoint]: ...
     def get_file_breaks(self, filename: str) -> List[Breakpoint]: ...
     def get_all_breaks(self) -> List[Breakpoint]: ...
-    def get_stack(self, f: Optional[FrameType], t: Optional[TracebackType]) -> Tuple[List[Tuple[FrameType, int]], int]: ...
+    def get_stack(self, f: FrameType | None, t: TracebackType | None) -> Tuple[List[Tuple[FrameType, int]], int]: ...
     def format_stack_entry(self, frame_lineno: int, lprefix: str = ...) -> str: ...
-    def run(
-        self, cmd: Union[str, CodeType], globals: Optional[Dict[str, Any]] = ..., locals: Optional[Mapping[str, Any]] = ...
-    ) -> None: ...
-    def runeval(self, expr: str, globals: Optional[Dict[str, Any]] = ..., locals: Optional[Mapping[str, Any]] = ...) -> None: ...
-    def runctx(
-        self, cmd: Union[str, CodeType], globals: Optional[Dict[str, Any]], locals: Optional[Mapping[str, Any]]
-    ) -> None: ...
-    def runcall(self, __func: Callable[..., _T], *args: Any, **kwds: Any) -> Optional[_T]: ...
+    def run(self, cmd: str | CodeType, globals: Dict[str, Any] | None = ..., locals: Mapping[str, Any] | None = ...) -> None: ...
+    def runeval(self, expr: str, globals: Dict[str, Any] | None = ..., locals: Mapping[str, Any] | None = ...) -> None: ...
+    def runctx(self, cmd: str | CodeType, globals: Dict[str, Any] | None, locals: Mapping[str, Any] | None) -> None: ...
+    def runcall(self, __func: Callable[..., _T], *args: Any, **kwds: Any) -> _T | None: ...
 
 class Breakpoint:
 
     next: int = ...
     bplist: Dict[Tuple[str, int], List[Breakpoint]] = ...
-    bpbynumber: List[Optional[Breakpoint]] = ...
+    bpbynumber: List[Breakpoint | None] = ...
 
-    funcname: Optional[str]
-    func_first_executable_line: Optional[int]
+    funcname: str | None
+    func_first_executable_line: int | None
     file: str
     line: int
     temporary: bool
-    cond: Optional[str]
+    cond: str | None
     enabled: bool
     ignore: int
     hits: int
     number: int
     def __init__(
-        self, file: str, line: int, temporary: bool = ..., cond: Optional[str] = ..., funcname: Optional[str] = ...
+        self, file: str, line: int, temporary: bool = ..., cond: str | None = ..., funcname: str | None = ...
     ) -> None: ...
     def deleteMe(self) -> None: ...
     def enable(self) -> None: ...
     def disable(self) -> None: ...
-    def bpprint(self, out: Optional[IO[str]] = ...) -> None: ...
+    def bpprint(self, out: IO[str] | None = ...) -> None: ...
     def bpformat(self) -> str: ...
     def __str__(self) -> str: ...
 
 def checkfuncname(b: Breakpoint, frame: FrameType) -> bool: ...
-def effective(file: str, line: int, frame: FrameType) -> Union[Tuple[Breakpoint, bool], Tuple[None, None]]: ...
+def effective(file: str, line: int, frame: FrameType) -> Tuple[Breakpoint, bool] | Tuple[None, None]: ...
 def set_trace() -> None: ...
diff --git a/stdlib/@python2/builtins.pyi b/stdlib/@python2/builtins.pyi
index 0b2c89e8d80c..ebe9cdd95038 100644
--- a/stdlib/@python2/builtins.pyi
+++ b/stdlib/@python2/builtins.pyi
@@ -26,7 +26,6 @@ from typing import (
     MutableSequence,
     MutableSet,
     NoReturn,
-    Optional,
     Protocol,
     Reversible,
     Sequence,
@@ -40,7 +39,6 @@ from typing import (
     Tuple,
     Type,
     TypeVar,
-    Union,
     ValuesView,
     overload,
 )
@@ -66,9 +64,9 @@ _TT = TypeVar("_TT", bound="type")
 _TBE = TypeVar("_TBE", bound="BaseException")
 
 class object:
-    __doc__: Optional[str]
+    __doc__: str | None
     __dict__: Dict[str, Any]
-    __slots__: Union[Text, Iterable[Text]]
+    __slots__: Text | Iterable[Text]
     __module__: str
     @property
     def __class__(self: _T) -> Type[_T]: ...
@@ -86,20 +84,20 @@ class object:
     def __getattribute__(self, name: str) -> Any: ...
     def __delattr__(self, name: str) -> None: ...
     def __sizeof__(self) -> int: ...
-    def __reduce__(self) -> Union[str, Tuple[Any, ...]]: ...
-    def __reduce_ex__(self, protocol: int) -> Union[str, Tuple[Any, ...]]: ...
+    def __reduce__(self) -> str | Tuple[Any, ...]: ...
+    def __reduce_ex__(self, protocol: int) -> str | Tuple[Any, ...]: ...
 
 class staticmethod(object):  # Special, only valid as a decorator.
     __func__: Callable[..., Any]
     def __init__(self, f: Callable[..., Any]) -> None: ...
     def __new__(cls: Type[_T], *args: Any, **kwargs: Any) -> _T: ...
-    def __get__(self, obj: _T, type: Optional[Type[_T]] = ...) -> Callable[..., Any]: ...
+    def __get__(self, obj: _T, type: Type[_T] | None = ...) -> Callable[..., Any]: ...
 
 class classmethod(object):  # Special, only valid as a decorator.
     __func__: Callable[..., Any]
     def __init__(self, f: Callable[..., Any]) -> None: ...
     def __new__(cls: Type[_T], *args: Any, **kwargs: Any) -> _T: ...
-    def __get__(self, obj: _T, type: Optional[Type[_T]] = ...) -> Callable[..., Any]: ...
+    def __get__(self, obj: _T, type: Type[_T] | None = ...) -> Callable[..., Any]: ...
 
 class type(object):
     __base__: type
@@ -137,9 +135,9 @@ class super(object):
 
 class int:
     @overload
-    def __new__(cls: Type[_T], x: Union[Text, bytes, SupportsInt, _SupportsIndex, _SupportsTrunc] = ...) -> _T: ...
+    def __new__(cls: Type[_T], x: Text | bytes | SupportsInt | _SupportsIndex | _SupportsTrunc = ...) -> _T: ...
     @overload
-    def __new__(cls: Type[_T], x: Union[Text, bytes, bytearray], base: int) -> _T: ...
+    def __new__(cls: Type[_T], x: Text | bytes | bytearray, base: int) -> _T: ...
     @property
     def real(self) -> int: ...
     @property
@@ -167,10 +165,10 @@ class int:
     def __rmod__(self, x: int) -> int: ...
     def __rdivmod__(self, x: int) -> Tuple[int, int]: ...
     @overload
-    def __pow__(self, __x: Literal[2], __modulo: Optional[int] = ...) -> int: ...
+    def __pow__(self, __x: Literal[2], __modulo: int | None = ...) -> int: ...
     @overload
-    def __pow__(self, __x: int, __modulo: Optional[int] = ...) -> Any: ...  # Return type can be int or float, depending on x.
-    def __rpow__(self, x: int, mod: Optional[int] = ...) -> Any: ...
+    def __pow__(self, __x: int, __modulo: int | None = ...) -> Any: ...  # Return type can be int or float, depending on x.
+    def __rpow__(self, x: int, mod: int | None = ...) -> Any: ...
     def __and__(self, n: int) -> int: ...
     def __or__(self, n: int) -> int: ...
     def __xor__(self, n: int) -> int: ...
@@ -201,7 +199,7 @@ class int:
     def __index__(self) -> int: ...
 
 class float:
-    def __new__(cls: Type[_T], x: Union[SupportsFloat, _SupportsIndex, Text, bytes, bytearray] = ...) -> _T: ...
+    def __new__(cls: Type[_T], x: SupportsFloat | _SupportsIndex | Text | bytes | bytearray = ...) -> _T: ...
     def as_integer_ratio(self) -> Tuple[int, int]: ...
     def hex(self) -> str: ...
     def is_integer(self) -> bool: ...
@@ -253,7 +251,7 @@ class complex:
     @overload
     def __new__(cls: Type[_T], real: float = ..., imag: float = ...) -> _T: ...
     @overload
-    def __new__(cls: Type[_T], real: Union[str, SupportsComplex, _SupportsIndex]) -> _T: ...
+    def __new__(cls: Type[_T], real: str | SupportsComplex | _SupportsIndex) -> _T: ...
     @property
     def real(self) -> float: ...
     @property
@@ -295,9 +293,7 @@ class unicode(basestring, Sequence[unicode]):
     def count(self, x: unicode) -> int: ...
     def decode(self, encoding: unicode = ..., errors: unicode = ...) -> unicode: ...
     def encode(self, encoding: unicode = ..., errors: unicode = ...) -> str: ...
-    def endswith(
-        self, __suffix: Union[unicode, Tuple[unicode, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def endswith(self, __suffix: unicode | Tuple[unicode, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def expandtabs(self, tabsize: int = ...) -> unicode: ...
     def find(self, sub: unicode, start: int = ..., end: int = ...) -> int: ...
     def format(self, *args: object, **kwargs: object) -> unicode: ...
@@ -323,17 +319,15 @@ class unicode(basestring, Sequence[unicode]):
     def rindex(self, sub: unicode, start: int = ..., end: int = ...) -> int: ...
     def rjust(self, width: int, fillchar: unicode = ...) -> unicode: ...
     def rpartition(self, sep: unicode) -> Tuple[unicode, unicode, unicode]: ...
-    def rsplit(self, sep: Optional[unicode] = ..., maxsplit: int = ...) -> List[unicode]: ...
+    def rsplit(self, sep: unicode | None = ..., maxsplit: int = ...) -> List[unicode]: ...
     def rstrip(self, chars: unicode = ...) -> unicode: ...
-    def split(self, sep: Optional[unicode] = ..., maxsplit: int = ...) -> List[unicode]: ...
+    def split(self, sep: unicode | None = ..., maxsplit: int = ...) -> List[unicode]: ...
     def splitlines(self, keepends: bool = ...) -> List[unicode]: ...
-    def startswith(
-        self, __prefix: Union[unicode, Tuple[unicode, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def startswith(self, __prefix: unicode | Tuple[unicode, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def strip(self, chars: unicode = ...) -> unicode: ...
     def swapcase(self) -> unicode: ...
     def title(self) -> unicode: ...
-    def translate(self, table: Union[Dict[int, Any], unicode]) -> unicode: ...
+    def translate(self, table: Dict[int, Any] | unicode) -> unicode: ...
     def upper(self) -> unicode: ...
     def zfill(self, width: int) -> unicode: ...
     @overload
@@ -353,7 +347,7 @@ class unicode(basestring, Sequence[unicode]):
     def __ge__(self, x: unicode) -> bool: ...
     def __len__(self) -> int: ...
     # The argument type is incompatible with Sequence
-    def __contains__(self, s: Union[unicode, bytes]) -> bool: ...  # type: ignore
+    def __contains__(self, s: unicode | bytes) -> bool: ...  # type: ignore
     def __iter__(self) -> Iterator[unicode]: ...
     def __str__(self) -> str: ...
     def __repr__(self) -> str: ...
@@ -369,17 +363,15 @@ class str(Sequence[str], basestring):
     def __init__(self, o: object = ...) -> None: ...
     def capitalize(self) -> str: ...
     def center(self, __width: int, __fillchar: str = ...) -> str: ...
-    def count(self, x: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def count(self, x: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def decode(self, encoding: Text = ..., errors: Text = ...) -> unicode: ...
     def encode(self, encoding: Text = ..., errors: Text = ...) -> bytes: ...
-    def endswith(
-        self, __suffix: Union[Text, Tuple[Text, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def endswith(self, __suffix: Text | Tuple[Text, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def expandtabs(self, tabsize: int = ...) -> str: ...
-    def find(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def find(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def format(self, *args: object, **kwargs: object) -> str: ...
     def format_map(self, map: _FormatMapMapping) -> str: ...
-    def index(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def index(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def isalnum(self) -> bool: ...
     def isalpha(self) -> bool: ...
     def isdigit(self) -> bool: ...
@@ -401,8 +393,8 @@ class str(Sequence[str], basestring):
     @overload
     def partition(self, __sep: unicode) -> Tuple[unicode, unicode, unicode]: ...
     def replace(self, __old: AnyStr, __new: AnyStr, __count: int = ...) -> AnyStr: ...
-    def rfind(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
-    def rindex(self, sub: Text, __start: Optional[int] = ..., __end: Optional[int] = ...) -> int: ...
+    def rfind(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
+    def rindex(self, sub: Text, __start: int | None = ..., __end: int | None = ...) -> int: ...
     def rjust(self, __width: int, __fillchar: str = ...) -> str: ...
     @overload
     def rpartition(self, __sep: bytearray) -> Tuple[str, bytearray, str]: ...
@@ -411,7 +403,7 @@ class str(Sequence[str], basestring):
     @overload
     def rpartition(self, __sep: unicode) -> Tuple[unicode, unicode, unicode]: ...
     @overload
-    def rsplit(self, sep: Optional[str] = ..., maxsplit: int = ...) -> List[str]: ...
+    def rsplit(self, sep: str | None = ..., maxsplit: int = ...) -> List[str]: ...
     @overload
     def rsplit(self, sep: unicode, maxsplit: int = ...) -> List[unicode]: ...
     @overload
@@ -419,28 +411,26 @@ class str(Sequence[str], basestring):
     @overload
     def rstrip(self, __chars: unicode) -> unicode: ...
     @overload
-    def split(self, sep: Optional[str] = ..., maxsplit: int = ...) -> List[str]: ...
+    def split(self, sep: str | None = ..., maxsplit: int = ...) -> List[str]: ...
     @overload
     def split(self, sep: unicode, maxsplit: int = ...) -> List[unicode]: ...
     def splitlines(self, keepends: bool = ...) -> List[str]: ...
-    def startswith(
-        self, __prefix: Union[Text, Tuple[Text, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def startswith(self, __prefix: Text | Tuple[Text, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     @overload
     def strip(self, __chars: str = ...) -> str: ...
     @overload
     def strip(self, chars: unicode) -> unicode: ...
     def swapcase(self) -> str: ...
     def title(self) -> str: ...
-    def translate(self, __table: Optional[AnyStr], deletechars: AnyStr = ...) -> AnyStr: ...
+    def translate(self, __table: AnyStr | None, deletechars: AnyStr = ...) -> AnyStr: ...
     def upper(self) -> str: ...
     def zfill(self, __width: int) -> str: ...
     def __add__(self, s: AnyStr) -> AnyStr: ...
     # Incompatible with Sequence.__contains__
-    def __contains__(self, o: Union[str, Text]) -> bool: ...  # type: ignore
+    def __contains__(self, o: str | Text) -> bool: ...  # type: ignore
     def __eq__(self, x: object) -> bool: ...
     def __ge__(self, x: Text) -> bool: ...
-    def __getitem__(self, i: Union[int, slice]) -> str: ...
+    def __getitem__(self, i: int | slice) -> str: ...
     def __gt__(self, x: Text) -> bool: ...
     def __hash__(self) -> int: ...
     def __iter__(self) -> Iterator[str]: ...
@@ -475,11 +465,9 @@ class bytearray(MutableSequence[int], ByteString):
     def center(self, __width: int, __fillchar: bytes = ...) -> bytearray: ...
     def count(self, __sub: str) -> int: ...
     def decode(self, encoding: Text = ..., errors: Text = ...) -> str: ...
-    def endswith(
-        self, __suffix: Union[bytes, Tuple[bytes, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
+    def endswith(self, __suffix: bytes | Tuple[bytes, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
     def expandtabs(self, tabsize: int = ...) -> bytearray: ...
-    def extend(self, iterable: Union[str, Iterable[int]]) -> None: ...
+    def extend(self, iterable: str | Iterable[int]) -> None: ...
     def find(self, __sub: str, __start: int = ..., __end: int = ...) -> int: ...
     def index(self, __sub: str, __start: int = ..., __end: int = ...) -> int: ...
     def insert(self, __index: int, __item: int) -> None: ...
@@ -493,21 +481,19 @@ class bytearray(MutableSequence[int], ByteString):
     def join(self, __iterable: Iterable[str]) -> bytearray: ...
     def ljust(self, __width: int, __fillchar: str = ...) -> bytearray: ...
     def lower(self) -> bytearray: ...
-    def lstrip(self, __bytes: Optional[bytes] = ...) -> bytearray: ...
+    def lstrip(self, __bytes: bytes | None = ...) -> bytearray: ...
     def partition(self, __sep: bytes) -> Tuple[bytearray, bytearray, bytearray]: ...
     def replace(self, __old: bytes, __new: bytes, __count: int = ...) -> bytearray: ...
     def rfind(self, __sub: bytes, __start: int = ..., __end: int = ...) -> int: ...
     def rindex(self, __sub: bytes, __start: int = ..., __end: int = ...) -> int: ...
     def rjust(self, __width: int, __fillchar: bytes = ...) -> bytearray: ...
     def rpartition(self, __sep: bytes) -> Tuple[bytearray, bytearray, bytearray]: ...
-    def rsplit(self, sep: Optional[bytes] = ..., maxsplit: int = ...) -> List[bytearray]: ...
-    def rstrip(self, __bytes: Optional[bytes] = ...) -> bytearray: ...
-    def split(self, sep: Optional[bytes] = ..., maxsplit: int = ...) -> List[bytearray]: ...
+    def rsplit(self, sep: bytes | None = ..., maxsplit: int = ...) -> List[bytearray]: ...
+    def rstrip(self, __bytes: bytes | None = ...) -> bytearray: ...
+    def split(self, sep: bytes | None = ..., maxsplit: int = ...) -> List[bytearray]: ...
     def splitlines(self, keepends: bool = ...) -> List[bytearray]: ...
-    def startswith(
-        self, __prefix: Union[bytes, Tuple[bytes, ...]], __start: Optional[int] = ..., __end: Optional[int] = ...
-    ) -> bool: ...
-    def strip(self, __bytes: Optional[bytes] = ...) -> bytearray: ...
+    def startswith(self, __prefix: bytes | Tuple[bytes, ...], __start: int | None = ..., __end: int | None = ...) -> bool: ...
+    def strip(self, __bytes: bytes | None = ...) -> bytearray: ...
     def swapcase(self) -> bytearray: ...
     def title(self) -> bytearray: ...
     def translate(self, __table: str) -> bytearray: ...
@@ -529,15 +515,15 @@ class bytearray(MutableSequence[int], ByteString):
     @overload
     def __setitem__(self, i: int, x: int) -> None: ...
     @overload
-    def __setitem__(self, s: slice, x: Union[Iterable[int], bytes]) -> None: ...
-    def __delitem__(self, i: Union[int, slice]) -> None: ...
+    def __setitem__(self, s: slice, x: Iterable[int] | bytes) -> None: ...
+    def __delitem__(self, i: int | slice) -> None: ...
     def __getslice__(self, start: int, stop: int) -> bytearray: ...
-    def __setslice__(self, start: int, stop: int, x: Union[Sequence[int], str]) -> None: ...
+    def __setslice__(self, start: int, stop: int, x: Sequence[int] | str) -> None: ...
     def __delslice__(self, start: int, stop: int) -> None: ...
     def __add__(self, s: bytes) -> bytearray: ...
     def __mul__(self, n: int) -> bytearray: ...
     # Incompatible with Sequence.__contains__
-    def __contains__(self, o: Union[int, bytes]) -> bool: ...  # type: ignore
+    def __contains__(self, o: int | bytes) -> bool: ...  # type: ignore
     def __eq__(self, x: object) -> bool: ...
     def __ne__(self, x: object) -> bool: ...
     def __lt__(self, x: bytes) -> bool: ...
@@ -548,9 +534,9 @@ class bytearray(MutableSequence[int], ByteString):
 class memoryview(Sized, Container[str]):
     format: str
     itemsize: int
-    shape: Optional[Tuple[int, ...]]
-    strides: Optional[Tuple[int, ...]]
-    suboffsets: Optional[Tuple[int, ...]]
+    shape: Tuple[int, ...] | None
+    strides: Tuple[int, ...] | None
+    suboffsets: Tuple[int, ...] | None
     readonly: bool
     ndim: int
     def __init__(self, obj: ReadableBuffer) -> None: ...
@@ -662,7 +648,7 @@ class list(MutableSequence[_T], Generic[_T]):
     def __setitem__(self, i: int, o: _T) -> None: ...
     @overload
     def __setitem__(self, s: slice, o: Iterable[_T]) -> None: ...
-    def __delitem__(self, i: Union[int, slice]) -> None: ...
+    def __delitem__(self, i: int | slice) -> None: ...
     def __getslice__(self, start: int, stop: int) -> List[_T]: ...
     def __setslice__(self, start: int, stop: int, o: Sequence[_T]) -> None: ...
     def __delslice__(self, start: int, stop: int) -> None: ...
@@ -743,18 +729,18 @@ class set(MutableSet[_T], Generic[_T]):
     def __str__(self) -> str: ...
     def __and__(self, s: AbstractSet[object]) -> Set[_T]: ...
     def __iand__(self, s: AbstractSet[object]) -> Set[_T]: ...
-    def __or__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
-    def __ior__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
+    def __or__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
+    def __ior__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
     @overload
-    def __sub__(self: Set[str], s: AbstractSet[Optional[Text]]) -> Set[_T]: ...
+    def __sub__(self: Set[str], s: AbstractSet[Text | None]) -> Set[_T]: ...
     @overload
-    def __sub__(self, s: AbstractSet[Optional[_T]]) -> Set[_T]: ...
+    def __sub__(self, s: AbstractSet[_T | None]) -> Set[_T]: ...
     @overload  # type: ignore
-    def __isub__(self: Set[str], s: AbstractSet[Optional[Text]]) -> Set[_T]: ...
+    def __isub__(self: Set[str], s: AbstractSet[Text | None]) -> Set[_T]: ...
     @overload
-    def __isub__(self, s: AbstractSet[Optional[_T]]) -> Set[_T]: ...
-    def __xor__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
-    def __ixor__(self, s: AbstractSet[_S]) -> Set[Union[_T, _S]]: ...
+    def __isub__(self, s: AbstractSet[_T | None]) -> Set[_T]: ...
+    def __xor__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
+    def __ixor__(self, s: AbstractSet[_S]) -> Set[_T | _S]: ...
     def __le__(self, s: AbstractSet[object]) -> bool: ...
     def __lt__(self, s: AbstractSet[object]) -> bool: ...
     def __ge__(self, s: AbstractSet[object]) -> bool: ...
@@ -776,9 +762,9 @@ class frozenset(AbstractSet[_T_co], Generic[_T_co]):
     def __iter__(self) -> Iterator[_T_co]: ...
     def __str__(self) -> str: ...
     def __and__(self, s: AbstractSet[_T_co]) -> FrozenSet[_T_co]: ...
-    def __or__(self, s: AbstractSet[_S]) -> FrozenSet[Union[_T_co, _S]]: ...
+    def __or__(self, s: AbstractSet[_S]) -> FrozenSet[_T_co | _S]: ...
     def __sub__(self, s: AbstractSet[_T_co]) -> FrozenSet[_T_co]: ...
-    def __xor__(self, s: AbstractSet[_S]) -> FrozenSet[Union[_T_co, _S]]: ...
+    def __xor__(self, s: AbstractSet[_S]) -> FrozenSet[_T_co | _S]: ...
     def __le__(self, s: AbstractSet[object]) -> bool: ...
     def __lt__(self, s: AbstractSet[object]) -> bool: ...
     def __ge__(self, s: AbstractSet[object]) -> bool: ...
@@ -802,15 +788,15 @@ class xrange(Sized, Iterable[int], Reversible[int]):
 class property(object):
     def __init__(
         self,
-        fget: Optional[Callable[[Any], Any]] = ...,
-        fset: Optional[Callable[[Any, Any], None]] = ...,
-        fdel: Optional[Callable[[Any], None]] = ...,
-        doc: Optional[str] = ...,
+        fget: Callable[[Any], Any] | None = ...,
+        fset: Callable[[Any, Any], None] | None = ...,
+        fdel: Callable[[Any], None] | None = ...,
+        doc: str | None = ...,
     ) -> None: ...
     def getter(self, fget: Callable[[Any], Any]) -> property: ...
     def setter(self, fset: Callable[[Any, Any], None]) -> property: ...
     def deleter(self, fdel: Callable[[Any], None]) -> property: ...
-    def __get__(self, obj: Any, type: Optional[type] = ...) -> Any: ...
+    def __get__(self, obj: Any, type: type | None = ...) -> Any: ...
     def __set__(self, obj: Any, value: Any) -> None: ...
     def __delete__(self, obj: Any) -> None: ...
     def fget(self) -> Any: ...
@@ -829,8 +815,8 @@ NotImplemented: _NotImplementedType
 def abs(__x: SupportsAbs[_T]) -> _T: ...
 def all(__iterable: Iterable[object]) -> bool: ...
 def any(__iterable: Iterable[object]) -> bool: ...
-def apply(__func: Callable[..., _T], __args: Optional[Sequence[Any]] = ..., __kwds: Optional[Mapping[str, Any]] = ...) -> _T: ...
-def bin(__number: Union[int, _SupportsIndex]) -> str: ...
+def apply(__func: Callable[..., _T], __args: Sequence[Any] | None = ..., __kwds: Mapping[str, Any] | None = ...) -> _T: ...
+def bin(__number: int | _SupportsIndex) -> str: ...
 def callable(__obj: object) -> bool: ...
 def chr(__i: int) -> str: ...
 def cmp(__x: Any, __y: Any) -> int: ...
@@ -838,7 +824,7 @@ def cmp(__x: Any, __y: Any) -> int: ...
 _N1 = TypeVar("_N1", bool, int, float, complex)
 
 def coerce(__x: _N1, __y: _N1) -> Tuple[_N1, _N1]: ...
-def compile(source: Union[Text, mod], filename: Text, mode: Text, flags: int = ..., dont_inherit: int = ...) -> Any: ...
+def compile(source: Text | mod, filename: Text, mode: Text, flags: int = ..., dont_inherit: int = ...) -> Any: ...
 def delattr(__obj: Any, __name: Text) -> None: ...
 def dir(__o: object = ...) -> List[str]: ...
 
@@ -846,18 +832,18 @@ _N2 = TypeVar("_N2", int, float)
 
 def divmod(__x: _N2, __y: _N2) -> Tuple[_N2, _N2]: ...
 def eval(
-    __source: Union[Text, bytes, CodeType], __globals: Optional[Dict[str, Any]] = ..., __locals: Optional[Mapping[str, Any]] = ...
+    __source: Text | bytes | CodeType, __globals: Dict[str, Any] | None = ..., __locals: Mapping[str, Any] | None = ...
 ) -> Any: ...
-def execfile(__filename: str, __globals: Optional[Dict[str, Any]] = ..., __locals: Optional[Dict[str, Any]] = ...) -> None: ...
+def execfile(__filename: str, __globals: Dict[str, Any] | None = ..., __locals: Dict[str, Any] | None = ...) -> None: ...
 def exit(code: object = ...) -> NoReturn: ...
 @overload
 def filter(__function: Callable[[AnyStr], Any], __iterable: AnyStr) -> AnyStr: ...  # type: ignore
 @overload
-def filter(__function: None, __iterable: Tuple[Optional[_T], ...]) -> Tuple[_T, ...]: ...  # type: ignore
+def filter(__function: None, __iterable: Tuple[_T | None, ...]) -> Tuple[_T, ...]: ...  # type: ignore
 @overload
 def filter(__function: Callable[[_T], Any], __iterable: Tuple[_T, ...]) -> Tuple[_T, ...]: ...  # type: ignore
 @overload
-def filter(__function: None, __iterable: Iterable[Optional[_T]]) -> List[_T]: ...
+def filter(__function: None, __iterable: Iterable[_T | None]) -> List[_T]: ...
 @overload
 def filter(__function: Callable[[_T], Any], __iterable: Iterable[_T]) -> List[_T]: ...
 def format(__value: object, __format_spec: str = ...) -> str: ...  # TODO unicode
@@ -867,26 +853,26 @@ def getattr(__o: Any, name: Text) -> Any: ...
 # While technically covered by the last overload, spelling out the types for None and bool
 # help mypy out in some tricky situations involving type context (aka bidirectional inference)
 @overload
-def getattr(__o: Any, name: Text, __default: None) -> Optional[Any]: ...
+def getattr(__o: Any, name: Text, __default: None) -> Any | None: ...
 @overload
-def getattr(__o: Any, name: Text, __default: bool) -> Union[Any, bool]: ...
+def getattr(__o: Any, name: Text, __default: bool) -> Any | bool: ...
 @overload
-def getattr(__o: Any, name: Text, __default: _T) -> Union[Any, _T]: ...
+def getattr(__o: Any, name: Text, __default: _T) -> Any | _T: ...
 def globals() -> Dict[str, Any]: ...
 def hasattr(__obj: Any, __name: Text) -> bool: ...
 def hash(__obj: object) -> int: ...
-def hex(__number: Union[int, _SupportsIndex]) -> str: ...
+def hex(__number: int | _SupportsIndex) -> str: ...
 def id(__obj: object) -> int: ...
 def input(__prompt: Any = ...) -> Any: ...
 def intern(__string: str) -> str: ...
 @overload
 def iter(__iterable: Iterable[_T]) -> Iterator[_T]: ...
 @overload
-def iter(__function: Callable[[], Optional[_T]], __sentinel: None) -> Iterator[_T]: ...
+def iter(__function: Callable[[], _T | None], __sentinel: None) -> Iterator[_T]: ...
 @overload
 def iter(__function: Callable[[], _T], __sentinel: Any) -> Iterator[_T]: ...
-def isinstance(__obj: object, __class_or_tuple: Union[type, Tuple[Union[type, Tuple[Any, ...]], ...]]) -> bool: ...
-def issubclass(__cls: type, __class_or_tuple: Union[type, Tuple[Union[type, Tuple[Any, ...]], ...]]) -> bool: ...
+def isinstance(__obj: object, __class_or_tuple: type | Tuple[type | Tuple[Any, ...], ...]) -> bool: ...
+def issubclass(__cls: type, __class_or_tuple: type | Tuple[type | Tuple[Any, ...], ...]) -> bool: ...
 def len(__obj: Sized) -> int: ...
 def locals() -> Dict[str, Any]: ...
 @overload
@@ -966,15 +952,13 @@ def min(__iterable: Iterable[_T], *, key: Callable[[_T], Any] = ...) -> _T: ...
 @overload
 def next(__i: Iterator[_T]) -> _T: ...
 @overload
-def next(__i: Iterator[_T], default: _VT) -> Union[_T, _VT]: ...
-def oct(__number: Union[int, _SupportsIndex]) -> str: ...
-def open(name: Union[unicode, int], mode: unicode = ..., buffering: int = ...) -> BinaryIO: ...
-def ord(__c: Union[Text, bytes]) -> int: ...
+def next(__i: Iterator[_T], default: _VT) -> _T | _VT: ...
+def oct(__number: int | _SupportsIndex) -> str: ...
+def open(name: unicode | int, mode: unicode = ..., buffering: int = ...) -> BinaryIO: ...
+def ord(__c: Text | bytes) -> int: ...
 
 # This is only available after from __future__ import print_function.
-def print(
-    *values: object, sep: Optional[Text] = ..., end: Optional[Text] = ..., file: Optional[SupportsWrite[Any]] = ...
-) -> None: ...
+def print(*values: object, sep: Text | None = ..., end: Text | None = ..., file: SupportsWrite[Any] | None = ...) -> None: ...
 
 _E = TypeVar("_E", contravariant=True)
 _M = TypeVar("_M", contravariant=True)
@@ -1018,12 +1002,12 @@ def round(number: SupportsFloat) -> float: ...
 def round(number: SupportsFloat, ndigits: int) -> float: ...
 def setattr(__obj: Any, __name: Text, __value: Any) -> None: ...
 def sorted(
-    __iterable: Iterable[_T], *, cmp: Callable[[_T, _T], int] = ..., key: Optional[Callable[[_T], Any]] = ..., reverse: bool = ...
+    __iterable: Iterable[_T], *, cmp: Callable[[_T, _T], int] = ..., key: Callable[[_T], Any] | None = ..., reverse: bool = ...
 ) -> List[_T]: ...
 @overload
-def sum(__iterable: Iterable[_T]) -> Union[_T, int]: ...
+def sum(__iterable: Iterable[_T]) -> _T | int: ...
 @overload
-def sum(__iterable: Iterable[_T], __start: _S) -> Union[_T, _S]: ...
+def sum(__iterable: Iterable[_T], __start: _S) -> _T | _S: ...
 def unichr(__i: int) -> unicode: ...
 def vars(__object: Any = ...) -> Dict[str, Any]: ...
 @overload
@@ -1052,8 +1036,8 @@ def zip(
 ) -> List[Tuple[Any, ...]]: ...
 def __import__(
     name: Text,
-    globals: Optional[Mapping[str, Any]] = ...,
-    locals: Optional[Mapping[str, Any]] = ...,
+    globals: Mapping[str, Any] | None = ...,
+    locals: Mapping[str, Any] | None = ...,
     fromlist: Sequence[str] = ...,
     level: int = ...,
 ) -> Any: ...
@@ -1071,7 +1055,7 @@ class buffer(Sized):
     def __init__(self, object: _AnyBuffer, offset: int = ..., size: int = ...) -> None: ...
     def __add__(self, other: _AnyBuffer) -> str: ...
     def __cmp__(self, other: _AnyBuffer) -> bool: ...
-    def __getitem__(self, key: Union[int, slice]) -> str: ...
+    def __getitem__(self, key: int | slice) -> str: ...
     def __getslice__(self, i: int, j: int) -> str: ...
     def __len__(self) -> int: ...
     def __mul__(self, x: int) -> str: ...
@@ -1119,10 +1103,10 @@ class RuntimeError(_StandardError): ...
 
 class SyntaxError(_StandardError):
     msg: str
-    lineno: Optional[int]
-    offset: Optional[int]
-    text: Optional[str]
-    filename: Optional[str]
+    lineno: int | None
+    offset: int | None
+    text: str | None
+    filename: str | None
 
 class SystemError(_StandardError): ...
 class TypeError(_StandardError): ...
@@ -1181,9 +1165,7 @@ class file(BinaryIO):
     def next(self) -> str: ...
     def read(self, n: int = ...) -> str: ...
     def __enter__(self) -> BinaryIO: ...
-    def __exit__(
-        self, t: Optional[type] = ..., exc: Optional[BaseException] = ..., tb: Optional[Any] = ...
-    ) -> Optional[bool]: ...
+    def __exit__(self, t: type | None = ..., exc: BaseException | None = ..., tb: Any | None = ...) -> bool | None: ...
     def flush(self) -> None: ...
     def fileno(self) -> int: ...
     def isatty(self) -> bool: ...
@@ -1197,4 +1179,4 @@ class file(BinaryIO):
     def readlines(self, hint: int = ...) -> List[str]: ...
     def write(self, data: str) -> int: ...
     def writelines(self, data: Iterable[str]) -> None: ...
-    def truncate(self, pos: Optional[int] = ...) -> int: ...
+    def truncate(self, pos: int | None = ...) -> int: ...
diff --git a/stdlib/@python2/bz2.pyi b/stdlib/@python2/bz2.pyi
index d3c0baded59a..81ee6f6ce26a 100644
--- a/stdlib/@python2/bz2.pyi
+++ b/stdlib/@python2/bz2.pyi
@@ -1,6 +1,6 @@
 import io
 from _typeshed import ReadableBuffer, WriteableBuffer
-from typing import IO, Any, Iterable, List, Optional, Text, TypeVar, Union
+from typing import IO, Any, Iterable, List, Text, TypeVar, Union
 from typing_extensions import SupportsIndex
 
 _PathOrFile = Union[Text, IO[bytes]]
@@ -11,10 +11,8 @@ def decompress(data: bytes) -> bytes: ...
 
 class BZ2File(io.BufferedIOBase, IO[bytes]):
     def __enter__(self: _T) -> _T: ...
-    def __init__(
-        self, filename: _PathOrFile, mode: str = ..., buffering: Optional[Any] = ..., compresslevel: int = ...
-    ) -> None: ...
-    def read(self, size: Optional[int] = ...) -> bytes: ...
+    def __init__(self, filename: _PathOrFile, mode: str = ..., buffering: Any | None = ..., compresslevel: int = ...) -> None: ...
+    def read(self, size: int | None = ...) -> bytes: ...
     def read1(self, size: int = ...) -> bytes: ...
     def readline(self, size: SupportsIndex = ...) -> bytes: ...  # type: ignore
     def readinto(self, b: WriteableBuffer) -> int: ...
diff --git a/stdlib/@python2/cProfile.pyi b/stdlib/@python2/cProfile.pyi
index 0cc2e94986fc..1257b0cc92eb 100644
--- a/stdlib/@python2/cProfile.pyi
+++ b/stdlib/@python2/cProfile.pyi
@@ -1,9 +1,9 @@
 from types import CodeType
-from typing import Any, Callable, Dict, Optional, Text, Tuple, TypeVar, Union
+from typing import Any, Callable, Dict, Text, Tuple, TypeVar
 
-def run(statement: str, filename: Optional[str] = ..., sort: Union[str, int] = ...) -> None: ...
+def run(statement: str, filename: str | None = ..., sort: str | int = ...) -> None: ...
 def runctx(
-    statement: str, globals: Dict[str, Any], locals: Dict[str, Any], filename: Optional[str] = ..., sort: Union[str, int] = ...
+    statement: str, globals: Dict[str, Any], locals: Dict[str, Any], filename: str | None = ..., sort: str | int = ...
 ) -> None: ...
 
 _SelfT = TypeVar("_SelfT", bound=Profile)
@@ -17,7 +17,7 @@ class Profile:
     ) -> None: ...
     def enable(self) -> None: ...
     def disable(self) -> None: ...
-    def print_stats(self, sort: Union[str, int] = ...) -> None: ...
+    def print_stats(self, sort: str | int = ...) -> None: ...
     def dump_stats(self, file: Text) -> None: ...
     def create_stats(self) -> None: ...
     def snapshot_stats(self) -> None: ...
@@ -25,4 +25,4 @@ class Profile:
     def runctx(self: _SelfT, cmd: str, globals: Dict[str, Any], locals: Dict[str, Any]) -> _SelfT: ...
     def runcall(self, __func: Callable[..., _T], *args: Any, **kw: Any) -> _T: ...
 
-def label(code: Union[str, CodeType]) -> _Label: ...  # undocumented
+def label(code: str | CodeType) -> _Label: ...  # undocumented
diff --git a/stdlib/@python2/cStringIO.pyi b/stdlib/@python2/cStringIO.pyi
index 8518625fc1df..7703e030c332 100644
--- a/stdlib/@python2/cStringIO.pyi
+++ b/stdlib/@python2/cStringIO.pyi
@@ -1,5 +1,5 @@
 from abc import ABCMeta
-from typing import IO, Iterable, Iterator, List, Optional, Union, overload
+from typing import IO, Iterable, Iterator, List, overload
 
 # This class isn't actually abstract, but you can't instantiate it
 # directly, so we might as well treat it as abstract in the stub.
@@ -15,7 +15,7 @@ class InputType(IO[str], Iterator[str], metaclass=ABCMeta):
     def readlines(self, hint: int = ...) -> List[str]: ...
     def seek(self, offset: int, whence: int = ...) -> int: ...
     def tell(self) -> int: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def __iter__(self) -> InputType: ...
     def next(self) -> str: ...
     def reset(self) -> None: ...
@@ -34,12 +34,12 @@ class OutputType(IO[str], Iterator[str], metaclass=ABCMeta):
     def readlines(self, hint: int = ...) -> List[str]: ...
     def seek(self, offset: int, whence: int = ...) -> int: ...
     def tell(self) -> int: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def __iter__(self) -> OutputType: ...
     def next(self) -> str: ...
     def reset(self) -> None: ...
-    def write(self, b: Union[str, unicode]) -> int: ...
-    def writelines(self, lines: Iterable[Union[str, unicode]]) -> None: ...
+    def write(self, b: str | unicode) -> int: ...
+    def writelines(self, lines: Iterable[str | unicode]) -> None: ...
 
 @overload
 def StringIO() -> OutputType: ...
diff --git a/stdlib/@python2/calendar.pyi b/stdlib/@python2/calendar.pyi
index 1a8cb1657f1b..ce765210dc1e 100644
--- a/stdlib/@python2/calendar.pyi
+++ b/stdlib/@python2/calendar.pyi
@@ -1,6 +1,6 @@
 import datetime
 from time import struct_time
-from typing import Any, Iterable, List, Optional, Sequence, Tuple, Union
+from typing import Any, Iterable, List, Optional, Sequence, Tuple
 
 _LocaleType = Tuple[Optional[str], Optional[str]]
 
@@ -63,7 +63,7 @@ class HTMLCalendar(Calendar):
     def formatmonthname(self, theyear: int, themonth: int, withyear: bool = ...) -> str: ...
     def formatmonth(self, theyear: int, themonth: int, withyear: bool = ...) -> str: ...
     def formatyear(self, theyear: int, width: int = ...) -> str: ...
-    def formatyearpage(self, theyear: int, width: int = ..., css: Optional[str] = ..., encoding: Optional[str] = ...) -> str: ...
+    def formatyearpage(self, theyear: int, width: int = ..., css: str | None = ..., encoding: str | None = ...) -> str: ...
 
 class TimeEncoding:
     def __init__(self, locale: _LocaleType) -> None: ...
@@ -71,12 +71,12 @@ class TimeEncoding:
     def __exit__(self, *args: Any) -> None: ...
 
 class LocaleTextCalendar(TextCalendar):
-    def __init__(self, firstweekday: int = ..., locale: Optional[_LocaleType] = ...) -> None: ...
+    def __init__(self, firstweekday: int = ..., locale: _LocaleType | None = ...) -> None: ...
     def formatweekday(self, day: int, width: int) -> str: ...
     def formatmonthname(self, theyear: int, themonth: int, width: int, withyear: bool = ...) -> str: ...
 
 class LocaleHTMLCalendar(HTMLCalendar):
-    def __init__(self, firstweekday: int = ..., locale: Optional[_LocaleType] = ...) -> None: ...
+    def __init__(self, firstweekday: int = ..., locale: _LocaleType | None = ...) -> None: ...
     def formatweekday(self, day: int) -> str: ...
     def formatmonthname(self, theyear: int, themonth: int, withyear: bool = ...) -> str: ...
 
@@ -85,7 +85,7 @@ c: TextCalendar
 def setfirstweekday(firstweekday: int) -> None: ...
 def format(cols: int, colwidth: int = ..., spacing: int = ...) -> str: ...
 def formatstring(cols: int, colwidth: int = ..., spacing: int = ...) -> str: ...
-def timegm(tuple: Union[Tuple[int, ...], struct_time]) -> int: ...
+def timegm(tuple: Tuple[int, ...] | struct_time) -> int: ...
 
 # Data attributes
 day_name: Sequence[str]
diff --git a/stdlib/@python2/cgi.pyi b/stdlib/@python2/cgi.pyi
index c3519bba9b20..674748242ebb 100644
--- a/stdlib/@python2/cgi.pyi
+++ b/stdlib/@python2/cgi.pyi
@@ -1,12 +1,12 @@
 from _typeshed import SupportsGetItem, SupportsItemAccess
 from builtins import type as _type
-from typing import IO, Any, AnyStr, Iterable, Iterator, List, Mapping, Optional, Protocol, TypeVar, Union
+from typing import IO, Any, AnyStr, Iterable, Iterator, List, Mapping, Protocol, TypeVar
 from UserDict import UserDict
 
 _T = TypeVar("_T", bound=FieldStorage)
 
 def parse(
-    fp: Optional[IO[Any]] = ...,
+    fp: IO[Any] | None = ...,
     environ: SupportsItemAccess[str, str] = ...,
     keep_blank_values: bool = ...,
     strict_parsing: bool = ...,
@@ -32,7 +32,7 @@ class MiniFieldStorage:
     filename: Any
     list: Any
     type: Any
-    file: Optional[IO[bytes]]
+    file: IO[bytes] | None
     type_options: dict[Any, Any]
     disposition: Any
     disposition_options: dict[Any, Any]
@@ -43,28 +43,28 @@ class MiniFieldStorage:
     def __repr__(self) -> str: ...
 
 class FieldStorage(object):
-    FieldStorageClass: Optional[_type]
+    FieldStorageClass: _type | None
     keep_blank_values: int
     strict_parsing: int
-    qs_on_post: Optional[str]
+    qs_on_post: str | None
     headers: Mapping[str, str]
     fp: IO[bytes]
     encoding: str
     errors: str
     outerboundary: bytes
     bytes_read: int
-    limit: Optional[int]
+    limit: int | None
     disposition: str
     disposition_options: dict[str, str]
-    filename: Optional[str]
-    file: Optional[IO[bytes]]
+    filename: str | None
+    file: IO[bytes] | None
     type: str
     type_options: dict[str, str]
     innerboundary: bytes
     length: int
     done: int
-    list: Optional[List[Any]]
-    value: Union[None, bytes, List[Any]]
+    list: List[Any] | None
+    value: None | bytes | List[Any]
     def __init__(
         self,
         fp: IO[Any] = ...,
diff --git a/stdlib/@python2/cgitb.pyi b/stdlib/@python2/cgitb.pyi
index 017840dc472c..daa0233ee69a 100644
--- a/stdlib/@python2/cgitb.pyi
+++ b/stdlib/@python2/cgitb.pyi
@@ -7,26 +7,19 @@ def reset() -> str: ...  # undocumented
 def small(text: str) -> str: ...  # undocumented
 def strong(text: str) -> str: ...  # undocumented
 def grey(text: str) -> str: ...  # undocumented
-def lookup(name: str, frame: FrameType, locals: Dict[str, Any]) -> Tuple[Optional[str], Any]: ...  # undocumented
+def lookup(name: str, frame: FrameType, locals: Dict[str, Any]) -> Tuple[str | None, Any]: ...  # undocumented
 def scanvars(
     reader: Callable[[], bytes], frame: FrameType, locals: Dict[str, Any]
-) -> List[Tuple[str, Optional[str], Any]]: ...  # undocumented
+) -> List[Tuple[str, str | None, Any]]: ...  # undocumented
 def html(einfo: _ExcInfo, context: int = ...) -> str: ...
 def text(einfo: _ExcInfo, context: int = ...) -> str: ...
 
 class Hook:  # undocumented
     def __init__(
-        self,
-        display: int = ...,
-        logdir: Optional[Text] = ...,
-        context: int = ...,
-        file: Optional[IO[str]] = ...,
-        format: str = ...,
+        self, display: int = ..., logdir: Text | None = ..., context: int = ..., file: IO[str] | None = ..., format: str = ...
     ) -> None: ...
-    def __call__(
-        self, etype: Optional[Type[BaseException]], evalue: Optional[BaseException], etb: Optional[TracebackType]
-    ) -> None: ...
-    def handle(self, info: Optional[_ExcInfo] = ...) -> None: ...
+    def __call__(self, etype: Type[BaseException] | None, evalue: BaseException | None, etb: TracebackType | None) -> None: ...
+    def handle(self, info: _ExcInfo | None = ...) -> None: ...
 
-def handler(info: Optional[_ExcInfo] = ...) -> None: ...
-def enable(display: int = ..., logdir: Optional[Text] = ..., context: int = ..., format: str = ...) -> None: ...
+def handler(info: _ExcInfo | None = ...) -> None: ...
+def enable(display: int = ..., logdir: Text | None = ..., context: int = ..., format: str = ...) -> None: ...
diff --git a/stdlib/@python2/cmd.pyi b/stdlib/@python2/cmd.pyi
index 0b7a7f704a9b..ffccba84ec16 100644
--- a/stdlib/@python2/cmd.pyi
+++ b/stdlib/@python2/cmd.pyi
@@ -1,11 +1,11 @@
-from typing import IO, Any, Callable, List, Optional, Tuple
+from typing import IO, Any, Callable, List, Tuple
 
 class Cmd:
     prompt: str
     identchars: str
     ruler: str
     lastcmd: str
-    intro: Optional[Any]
+    intro: Any | None
     doc_leader: str
     doc_header: str
     misc_header: str
@@ -16,24 +16,24 @@ class Cmd:
     stdout: IO[str]
     cmdqueue: List[str]
     completekey: str
-    def __init__(self, completekey: str = ..., stdin: Optional[IO[str]] = ..., stdout: Optional[IO[str]] = ...) -> None: ...
-    old_completer: Optional[Callable[[str, int], Optional[str]]]
-    def cmdloop(self, intro: Optional[Any] = ...) -> None: ...
+    def __init__(self, completekey: str = ..., stdin: IO[str] | None = ..., stdout: IO[str] | None = ...) -> None: ...
+    old_completer: Callable[[str, int], str | None] | None
+    def cmdloop(self, intro: Any | None = ...) -> None: ...
     def precmd(self, line: str) -> str: ...
     def postcmd(self, stop: bool, line: str) -> bool: ...
     def preloop(self) -> None: ...
     def postloop(self) -> None: ...
-    def parseline(self, line: str) -> Tuple[Optional[str], Optional[str], str]: ...
+    def parseline(self, line: str) -> Tuple[str | None, str | None, str]: ...
     def onecmd(self, line: str) -> bool: ...
     def emptyline(self) -> bool: ...
     def default(self, line: str) -> bool: ...
     def completedefault(self, *ignored: Any) -> List[str]: ...
     def completenames(self, text: str, *ignored: Any) -> List[str]: ...
-    completion_matches: Optional[List[str]]
-    def complete(self, text: str, state: int) -> Optional[List[str]]: ...
+    completion_matches: List[str] | None
+    def complete(self, text: str, state: int) -> List[str] | None: ...
     def get_names(self) -> List[str]: ...
     # Only the first element of args matters.
     def complete_help(self, *args: Any) -> List[str]: ...
-    def do_help(self, arg: str) -> Optional[bool]: ...
-    def print_topics(self, header: str, cmds: Optional[List[str]], cmdlen: Any, maxcol: int) -> None: ...
-    def columnize(self, list: Optional[List[str]], displaywidth: int = ...) -> None: ...
+    def do_help(self, arg: str) -> bool | None: ...
+    def print_topics(self, header: str, cmds: List[str] | None, cmdlen: Any, maxcol: int) -> None: ...
+    def columnize(self, list: List[str] | None, displaywidth: int = ...) -> None: ...
diff --git a/stdlib/@python2/code.pyi b/stdlib/@python2/code.pyi
index ea882c9de68e..ae8dfc91a32b 100644
--- a/stdlib/@python2/code.pyi
+++ b/stdlib/@python2/code.pyi
@@ -1,22 +1,22 @@
 from types import CodeType
-from typing import Any, Callable, Mapping, Optional
+from typing import Any, Callable, Mapping
 
 class InteractiveInterpreter:
-    def __init__(self, locals: Optional[Mapping[str, Any]] = ...) -> None: ...
+    def __init__(self, locals: Mapping[str, Any] | None = ...) -> None: ...
     def runsource(self, source: str, filename: str = ..., symbol: str = ...) -> bool: ...
     def runcode(self, code: CodeType) -> None: ...
-    def showsyntaxerror(self, filename: Optional[str] = ...) -> None: ...
+    def showsyntaxerror(self, filename: str | None = ...) -> None: ...
     def showtraceback(self) -> None: ...
     def write(self, data: str) -> None: ...
 
 class InteractiveConsole(InteractiveInterpreter):
-    def __init__(self, locals: Optional[Mapping[str, Any]] = ..., filename: str = ...) -> None: ...
-    def interact(self, banner: Optional[str] = ...) -> None: ...
+    def __init__(self, locals: Mapping[str, Any] | None = ..., filename: str = ...) -> None: ...
+    def interact(self, banner: str | None = ...) -> None: ...
     def push(self, line: str) -> bool: ...
     def resetbuffer(self) -> None: ...
     def raw_input(self, prompt: str = ...) -> str: ...
 
 def interact(
-    banner: Optional[str] = ..., readfunc: Optional[Callable[[str], str]] = ..., local: Optional[Mapping[str, Any]] = ...
+    banner: str | None = ..., readfunc: Callable[[str], str] | None = ..., local: Mapping[str, Any] | None = ...
 ) -> None: ...
-def compile_command(source: str, filename: str = ..., symbol: str = ...) -> Optional[CodeType]: ...
+def compile_command(source: str, filename: str = ..., symbol: str = ...) -> CodeType | None: ...
diff --git a/stdlib/@python2/codecs.pyi b/stdlib/@python2/codecs.pyi
index 8bacab771b0d..a7835106336d 100644
--- a/stdlib/@python2/codecs.pyi
+++ b/stdlib/@python2/codecs.pyi
@@ -9,7 +9,6 @@ from typing import (
     Iterable,
     Iterator,
     List,
-    Optional,
     Protocol,
     Text,
     TextIO,
@@ -83,9 +82,9 @@ def decode(obj: str, encoding: Literal["rot13", "rot_13"] = ..., errors: str = .
 def decode(obj: _Encoded, encoding: str = ..., errors: str = ...) -> _Decoded: ...
 def lookup(__encoding: str) -> CodecInfo: ...
 def utf_16_be_decode(
-    __data: _Encoded, __errors: Optional[str] = ..., __final: bool = ...
+    __data: _Encoded, __errors: str | None = ..., __final: bool = ...
 ) -> Tuple[_Decoded, int]: ...  # undocumented
-def utf_16_be_encode(__str: _Decoded, __errors: Optional[str] = ...) -> Tuple[_Encoded, int]: ...  # undocumented
+def utf_16_be_encode(__str: _Decoded, __errors: str | None = ...) -> Tuple[_Encoded, int]: ...  # undocumented
 
 class CodecInfo(Tuple[_Encoder, _Decoder, _StreamReader, _StreamWriter]):
     @property
@@ -105,13 +104,13 @@ class CodecInfo(Tuple[_Encoder, _Decoder, _StreamReader, _StreamWriter]):
         cls,
         encode: _Encoder,
         decode: _Decoder,
-        streamreader: Optional[_StreamReader] = ...,
-        streamwriter: Optional[_StreamWriter] = ...,
-        incrementalencoder: Optional[_IncrementalEncoder] = ...,
-        incrementaldecoder: Optional[_IncrementalDecoder] = ...,
-        name: Optional[str] = ...,
+        streamreader: _StreamReader | None = ...,
+        streamwriter: _StreamWriter | None = ...,
+        incrementalencoder: _IncrementalEncoder | None = ...,
+        incrementaldecoder: _IncrementalDecoder | None = ...,
+        name: str | None = ...,
         *,
-        _is_text_encoding: Optional[bool] = ...,
+        _is_text_encoding: bool | None = ...,
     ) -> CodecInfo: ...
 
 def getencoder(encoding: str) -> _Encoder: ...
@@ -120,13 +119,11 @@ def getincrementalencoder(encoding: str) -> _IncrementalEncoder: ...
 def getincrementaldecoder(encoding: str) -> _IncrementalDecoder: ...
 def getreader(encoding: str) -> _StreamReader: ...
 def getwriter(encoding: str) -> _StreamWriter: ...
-def register(__search_function: Callable[[str], Optional[CodecInfo]]) -> None: ...
+def register(__search_function: Callable[[str], CodecInfo | None]) -> None: ...
 def open(
-    filename: str, mode: str = ..., encoding: Optional[str] = ..., errors: str = ..., buffering: int = ...
+    filename: str, mode: str = ..., encoding: str | None = ..., errors: str = ..., buffering: int = ...
 ) -> StreamReaderWriter: ...
-def EncodedFile(
-    file: IO[_Encoded], data_encoding: str, file_encoding: Optional[str] = ..., errors: str = ...
-) -> StreamRecoder: ...
+def EncodedFile(file: IO[_Encoded], data_encoding: str, file_encoding: str | None = ..., errors: str = ...) -> StreamRecoder: ...
 def iterencode(iterator: Iterable[_Decoded], encoding: str, errors: str = ...) -> Generator[_Encoded, None, None]: ...
 def iterdecode(iterator: Iterable[_Encoded], encoding: str, errors: str = ...) -> Generator[_Decoded, None, None]: ...
 
@@ -144,13 +141,13 @@ BOM_UTF32_LE: bytes
 # It is expected that different actions be taken depending on which of the
 # three subclasses of `UnicodeError` is actually ...ed. However, the Union
 # is still needed for at least one of the cases.
-def register_error(__errors: str, __handler: Callable[[UnicodeError], Tuple[Union[str, bytes], int]]) -> None: ...
-def lookup_error(__name: str) -> Callable[[UnicodeError], Tuple[Union[str, bytes], int]]: ...
-def strict_errors(exception: UnicodeError) -> Tuple[Union[str, bytes], int]: ...
-def replace_errors(exception: UnicodeError) -> Tuple[Union[str, bytes], int]: ...
-def ignore_errors(exception: UnicodeError) -> Tuple[Union[str, bytes], int]: ...
-def xmlcharrefreplace_errors(exception: UnicodeError) -> Tuple[Union[str, bytes], int]: ...
-def backslashreplace_errors(exception: UnicodeError) -> Tuple[Union[str, bytes], int]: ...
+def register_error(__errors: str, __handler: Callable[[UnicodeError], Tuple[str | bytes, int]]) -> None: ...
+def lookup_error(__name: str) -> Callable[[UnicodeError], Tuple[str | bytes, int]]: ...
+def strict_errors(exception: UnicodeError) -> Tuple[str | bytes, int]: ...
+def replace_errors(exception: UnicodeError) -> Tuple[str | bytes, int]: ...
+def ignore_errors(exception: UnicodeError) -> Tuple[str | bytes, int]: ...
+def xmlcharrefreplace_errors(exception: UnicodeError) -> Tuple[str | bytes, int]: ...
+def backslashreplace_errors(exception: UnicodeError) -> Tuple[str | bytes, int]: ...
 
 class Codec:
     # These are sort of @abstractmethod but sort of not.
@@ -165,8 +162,8 @@ class IncrementalEncoder:
     def encode(self, input: _Decoded, final: bool = ...) -> _Encoded: ...
     def reset(self) -> None: ...
     # documentation says int but str is needed for the subclass.
-    def getstate(self) -> Union[int, _Decoded]: ...
-    def setstate(self, state: Union[int, _Decoded]) -> None: ...
+    def getstate(self) -> int | _Decoded: ...
+    def setstate(self, state: int | _Decoded) -> None: ...
 
 class IncrementalDecoder:
     errors: str
@@ -203,9 +200,7 @@ class StreamWriter(Codec):
     def writelines(self, list: Iterable[_Decoded]) -> None: ...
     def reset(self) -> None: ...
     def __enter__(self: _SW) -> _SW: ...
-    def __exit__(
-        self, typ: Optional[Type[BaseException]], exc: Optional[BaseException], tb: Optional[types.TracebackType]
-    ) -> None: ...
+    def __exit__(self, typ: Type[BaseException] | None, exc: BaseException | None, tb: types.TracebackType | None) -> None: ...
     def __getattr__(self, name: str, getattr: Callable[[str], Any] = ...) -> Any: ...
 
 _SR = TypeVar("_SR", bound=StreamReader)
@@ -214,13 +209,11 @@ class StreamReader(Codec):
     errors: str
     def __init__(self, stream: IO[_Encoded], errors: str = ...) -> None: ...
     def read(self, size: int = ..., chars: int = ..., firstline: bool = ...) -> _Decoded: ...
-    def readline(self, size: Optional[int] = ..., keepends: bool = ...) -> _Decoded: ...
-    def readlines(self, sizehint: Optional[int] = ..., keepends: bool = ...) -> List[_Decoded]: ...
+    def readline(self, size: int | None = ..., keepends: bool = ...) -> _Decoded: ...
+    def readlines(self, sizehint: int | None = ..., keepends: bool = ...) -> List[_Decoded]: ...
     def reset(self) -> None: ...
     def __enter__(self: _SR) -> _SR: ...
-    def __exit__(
-        self, typ: Optional[Type[BaseException]], exc: Optional[BaseException], tb: Optional[types.TracebackType]
-    ) -> None: ...
+    def __exit__(self, typ: Type[BaseException] | None, exc: BaseException | None, tb: types.TracebackType | None) -> None: ...
     def __iter__(self) -> Iterator[_Decoded]: ...
     def __getattr__(self, name: str, getattr: Callable[[str], Any] = ...) -> Any: ...
 
@@ -231,8 +224,8 @@ _T = TypeVar("_T", bound=StreamReaderWriter)
 class StreamReaderWriter(TextIO):
     def __init__(self, stream: IO[_Encoded], Reader: _StreamReader, Writer: _StreamWriter, errors: str = ...) -> None: ...
     def read(self, size: int = ...) -> _Decoded: ...
-    def readline(self, size: Optional[int] = ...) -> _Decoded: ...
-    def readlines(self, sizehint: Optional[int] = ...) -> List[_Decoded]: ...
+    def readline(self, size: int | None = ...) -> _Decoded: ...
+    def readlines(self, sizehint: int | None = ...) -> List[_Decoded]: ...
     def next(self) -> Text: ...
     def __iter__(self: _T) -> _T: ...
     # This actually returns None, but that's incompatible with the supertype
@@ -242,9 +235,7 @@ class StreamReaderWriter(TextIO):
     # Same as write()
     def seek(self, offset: int, whence: int = ...) -> int: ...
     def __enter__(self: _T) -> _T: ...
-    def __exit__(
-        self, typ: Optional[Type[BaseException]], exc: Optional[BaseException], tb: Optional[types.TracebackType]
-    ) -> None: ...
+    def __exit__(self, typ: Type[BaseException] | None, exc: BaseException | None, tb: types.TracebackType | None) -> None: ...
     def __getattr__(self, name: str) -> Any: ...
     # These methods don't actually exist directly, but they are needed to satisfy the TextIO
     # interface. At runtime, they are delegated through __getattr__.
@@ -253,7 +244,7 @@ class StreamReaderWriter(TextIO):
     def flush(self) -> None: ...
     def isatty(self) -> bool: ...
     def readable(self) -> bool: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def seekable(self) -> bool: ...
     def tell(self) -> int: ...
     def writable(self) -> bool: ...
@@ -271,8 +262,8 @@ class StreamRecoder(BinaryIO):
         errors: str = ...,
     ) -> None: ...
     def read(self, size: int = ...) -> bytes: ...
-    def readline(self, size: Optional[int] = ...) -> bytes: ...
-    def readlines(self, sizehint: Optional[int] = ...) -> List[bytes]: ...
+    def readline(self, size: int | None = ...) -> bytes: ...
+    def readlines(self, sizehint: int | None = ...) -> List[bytes]: ...
     def next(self) -> bytes: ...
     def __iter__(self: _SRT) -> _SRT: ...
     def write(self, data: bytes) -> int: ...
@@ -280,9 +271,7 @@ class StreamRecoder(BinaryIO):
     def reset(self) -> None: ...
     def __getattr__(self, name: str) -> Any: ...
     def __enter__(self: _SRT) -> _SRT: ...
-    def __exit__(
-        self, type: Optional[Type[BaseException]], value: Optional[BaseException], tb: Optional[types.TracebackType]
-    ) -> None: ...
+    def __exit__(self, type: Type[BaseException] | None, value: BaseException | None, tb: types.TracebackType | None) -> None: ...
     # These methods don't actually exist directly, but they are needed to satisfy the BinaryIO
     # interface. At runtime, they are delegated through __getattr__.
     def seek(self, offset: int, whence: int = ...) -> int: ...
@@ -291,7 +280,7 @@ class StreamRecoder(BinaryIO):
     def flush(self) -> None: ...
     def isatty(self) -> bool: ...
     def readable(self) -> bool: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def seekable(self) -> bool: ...
     def tell(self) -> int: ...
     def writable(self) -> bool: ...
diff --git a/stdlib/@python2/codeop.pyi b/stdlib/@python2/codeop.pyi
index f3d6c2819ec6..8ed5710c9891 100644
--- a/stdlib/@python2/codeop.pyi
+++ b/stdlib/@python2/codeop.pyi
@@ -1,7 +1,6 @@
 from types import CodeType
-from typing import Optional
 
-def compile_command(source: str, filename: str = ..., symbol: str = ...) -> Optional[CodeType]: ...
+def compile_command(source: str, filename: str = ..., symbol: str = ...) -> CodeType | None: ...
 
 class Compile:
     flags: int
@@ -11,4 +10,4 @@ class Compile:
 class CommandCompiler:
     compiler: Compile
     def __init__(self) -> None: ...
-    def __call__(self, source: str, filename: str = ..., symbol: str = ...) -> Optional[CodeType]: ...
+    def __call__(self, source: str, filename: str = ..., symbol: str = ...) -> CodeType | None: ...
diff --git a/stdlib/@python2/collections.pyi b/stdlib/@python2/collections.pyi
index f6f75cb076c2..5a2f73aed7ce 100644
--- a/stdlib/@python2/collections.pyi
+++ b/stdlib/@python2/collections.pyi
@@ -16,14 +16,12 @@ from typing import (
     MutableMapping as MutableMapping,
     MutableSequence as MutableSequence,
     MutableSet as MutableSet,
-    Optional,
     Reversible,
     Sequence as Sequence,
     Sized as Sized,
     Tuple,
     Type,
     TypeVar,
-    Union,
     ValuesView as ValuesView,
     overload,
 )
@@ -37,16 +35,13 @@ _VT = TypeVar("_VT")
 
 # namedtuple is special-cased in the type checker; the initializer is ignored.
 def namedtuple(
-    typename: Union[str, unicode],
-    field_names: Union[str, unicode, Iterable[Union[str, unicode]]],
-    verbose: bool = ...,
-    rename: bool = ...,
+    typename: str | unicode, field_names: str | unicode | Iterable[str | unicode], verbose: bool = ..., rename: bool = ...
 ) -> Type[Tuple[Any, ...]]: ...
 
 class deque(Sized, Iterable[_T], Reversible[_T], Generic[_T]):
     def __init__(self, iterable: Iterable[_T] = ..., maxlen: int = ...) -> None: ...
     @property
-    def maxlen(self) -> Optional[int]: ...
+    def maxlen(self) -> int | None: ...
     def append(self, x: _T) -> None: ...
     def appendleft(self, x: _T) -> None: ...
     def clear(self) -> None: ...
@@ -77,7 +72,7 @@ class Counter(Dict[_T, int], Generic[_T]):
     def __init__(self, iterable: Iterable[_T]) -> None: ...
     def copy(self: _S) -> _S: ...
     def elements(self) -> Iterator[_T]: ...
-    def most_common(self, n: Optional[int] = ...) -> List[Tuple[_T, int]]: ...
+    def most_common(self, n: int | None = ...) -> List[Tuple[_T, int]]: ...
     @overload
     def subtract(self, __mapping: Mapping[_T, int]) -> None: ...
     @overload
@@ -90,7 +85,7 @@ class Counter(Dict[_T, int], Generic[_T]):
     @overload
     def update(self, __m: Mapping[_T, int], **kwargs: int) -> None: ...
     @overload
-    def update(self, __m: Union[Iterable[_T], Iterable[Tuple[_T, int]]], **kwargs: int) -> None: ...
+    def update(self, __m: Iterable[_T] | Iterable[Tuple[_T, int]], **kwargs: int) -> None: ...
     @overload
     def update(self, **kwargs: int) -> None: ...
     def __add__(self, other: Counter[_T]) -> Counter[_T]: ...
@@ -112,18 +107,16 @@ class defaultdict(Dict[_KT, _VT], Generic[_KT, _VT]):
     @overload
     def __init__(self, **kwargs: _VT) -> None: ...
     @overload
-    def __init__(self, default_factory: Optional[Callable[[], _VT]]) -> None: ...
+    def __init__(self, default_factory: Callable[[], _VT] | None) -> None: ...
     @overload
-    def __init__(self, default_factory: Optional[Callable[[], _VT]], **kwargs: _VT) -> None: ...
+    def __init__(self, default_factory: Callable[[], _VT] | None, **kwargs: _VT) -> None: ...
     @overload
-    def __init__(self, default_factory: Optional[Callable[[], _VT]], map: Mapping[_KT, _VT]) -> None: ...
+    def __init__(self, default_factory: Callable[[], _VT] | None, map: Mapping[_KT, _VT]) -> None: ...
     @overload
-    def __init__(self, default_factory: Optional[Callable[[], _VT]], map: Mapping[_KT, _VT], **kwargs: _VT) -> None: ...
+    def __init__(self, default_factory: Callable[[], _VT] | None, map: Mapping[_KT, _VT], **kwargs: _VT) -> None: ...
     @overload
-    def __init__(self, default_factory: Optional[Callable[[], _VT]], iterable: Iterable[Tuple[_KT, _VT]]) -> None: ...
+    def __init__(self, default_factory: Callable[[], _VT] | None, iterable: Iterable[Tuple[_KT, _VT]]) -> None: ...
     @overload
-    def __init__(
-        self, default_factory: Optional[Callable[[], _VT]], iterable: Iterable[Tuple[_KT, _VT]], **kwargs: _VT
-    ) -> None: ...
+    def __init__(self, default_factory: Callable[[], _VT] | None, iterable: Iterable[Tuple[_KT, _VT]], **kwargs: _VT) -> None: ...
     def __missing__(self, key: _KT) -> _VT: ...
     def copy(self: _S) -> _S: ...
diff --git a/stdlib/@python2/compileall.pyi b/stdlib/@python2/compileall.pyi
index 5ae1d6f7f7c1..ef22929c4c19 100644
--- a/stdlib/@python2/compileall.pyi
+++ b/stdlib/@python2/compileall.pyi
@@ -1,15 +1,10 @@
-from typing import Any, Optional, Pattern, Text
+from typing import Any, Pattern, Text
 
 # rx can be any object with a 'search' method; once we have Protocols we can change the type
 def compile_dir(
-    dir: Text,
-    maxlevels: int = ...,
-    ddir: Optional[Text] = ...,
-    force: bool = ...,
-    rx: Optional[Pattern[Any]] = ...,
-    quiet: int = ...,
+    dir: Text, maxlevels: int = ..., ddir: Text | None = ..., force: bool = ..., rx: Pattern[Any] | None = ..., quiet: int = ...
 ) -> int: ...
 def compile_file(
-    fullname: Text, ddir: Optional[Text] = ..., force: bool = ..., rx: Optional[Pattern[Any]] = ..., quiet: int = ...
+    fullname: Text, ddir: Text | None = ..., force: bool = ..., rx: Pattern[Any] | None = ..., quiet: int = ...
 ) -> int: ...
 def compile_path(skip_curdir: bool = ..., maxlevels: int = ..., force: bool = ..., quiet: int = ...) -> int: ...
diff --git a/stdlib/@python2/cookielib.pyi b/stdlib/@python2/cookielib.pyi
index 7405ba91c0ff..0f813c128cc4 100644
--- a/stdlib/@python2/cookielib.pyi
+++ b/stdlib/@python2/cookielib.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Optional
+from typing import Any
 
 class Cookie:
     version: Any
@@ -38,9 +38,9 @@ class Cookie:
         rfc2109: bool = ...,
     ): ...
     def has_nonstandard_attr(self, name): ...
-    def get_nonstandard_attr(self, name, default: Optional[Any] = ...): ...
+    def get_nonstandard_attr(self, name, default: Any | None = ...): ...
     def set_nonstandard_attr(self, name, value): ...
-    def is_expired(self, now: Optional[Any] = ...): ...
+    def is_expired(self, now: Any | None = ...): ...
 
 class CookiePolicy:
     def set_ok(self, cookie, request): ...
@@ -66,11 +66,11 @@ class DefaultCookiePolicy(CookiePolicy):
     strict_ns_set_path: Any
     def __init__(
         self,
-        blocked_domains: Optional[Any] = ...,
-        allowed_domains: Optional[Any] = ...,
+        blocked_domains: Any | None = ...,
+        allowed_domains: Any | None = ...,
         netscape: bool = ...,
         rfc2965: bool = ...,
-        rfc2109_as_netscape: Optional[Any] = ...,
+        rfc2109_as_netscape: Any | None = ...,
         hide_cookie2: bool = ...,
         strict_domain: bool = ...,
         strict_rfc2965_unverifiable: bool = ...,
@@ -111,14 +111,14 @@ class CookieJar:
     domain_re: Any
     dots_re: Any
     magic_re: Any
-    def __init__(self, policy: Optional[Any] = ...): ...
+    def __init__(self, policy: Any | None = ...): ...
     def set_policy(self, policy): ...
     def add_cookie_header(self, request): ...
     def make_cookies(self, response, request): ...
     def set_cookie_if_ok(self, cookie, request): ...
     def set_cookie(self, cookie): ...
     def extract_cookies(self, response, request): ...
-    def clear(self, domain: Optional[Any] = ..., path: Optional[Any] = ..., name: Optional[Any] = ...): ...
+    def clear(self, domain: Any | None = ..., path: Any | None = ..., name: Any | None = ...): ...
     def clear_session_cookies(self): ...
     def clear_expired_cookies(self): ...
     def __iter__(self): ...
@@ -129,10 +129,10 @@ class LoadError(IOError): ...
 class FileCookieJar(CookieJar):
     filename: Any
     delayload: Any
-    def __init__(self, filename: Optional[Any] = ..., delayload: bool = ..., policy: Optional[Any] = ...): ...
-    def save(self, filename: Optional[Any] = ..., ignore_discard: bool = ..., ignore_expires: bool = ...): ...
-    def load(self, filename: Optional[Any] = ..., ignore_discard: bool = ..., ignore_expires: bool = ...): ...
-    def revert(self, filename: Optional[Any] = ..., ignore_discard: bool = ..., ignore_expires: bool = ...): ...
+    def __init__(self, filename: Any | None = ..., delayload: bool = ..., policy: Any | None = ...): ...
+    def save(self, filename: Any | None = ..., ignore_discard: bool = ..., ignore_expires: bool = ...): ...
+    def load(self, filename: Any | None = ..., ignore_discard: bool = ..., ignore_expires: bool = ...): ...
+    def revert(self, filename: Any | None = ..., ignore_discard: bool = ..., ignore_expires: bool = ...): ...
 
 class LWPCookieJar(FileCookieJar):
     def as_lwp_str(self, ignore_discard: bool = ..., ignore_expires: bool = ...) -> str: ...  # undocumented
diff --git a/stdlib/@python2/copy.pyi b/stdlib/@python2/copy.pyi
index b51c79c66c6a..c88f92846ddf 100644
--- a/stdlib/@python2/copy.pyi
+++ b/stdlib/@python2/copy.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Dict, Optional, TypeVar
+from typing import Any, Dict, TypeVar
 
 _T = TypeVar("_T")
 
@@ -6,7 +6,7 @@ _T = TypeVar("_T")
 PyStringMap: Any
 
 # Note: memo and _nil are internal kwargs.
-def deepcopy(x: _T, memo: Optional[Dict[int, Any]] = ..., _nil: Any = ...) -> _T: ...
+def deepcopy(x: _T, memo: Dict[int, Any] | None = ..., _nil: Any = ...) -> _T: ...
 def copy(x: _T) -> _T: ...
 
 class Error(Exception): ...
diff --git a/stdlib/@python2/copy_reg.pyi b/stdlib/@python2/copy_reg.pyi
index ea07ba410b6d..91b099888bab 100644
--- a/stdlib/@python2/copy_reg.pyi
+++ b/stdlib/@python2/copy_reg.pyi
@@ -7,8 +7,8 @@ __all__: List[str]
 
 def pickle(
     ob_type: _TypeT,
-    pickle_function: Callable[[_TypeT], Union[str, _Reduce[_TypeT]]],
-    constructor_ob: Optional[Callable[[_Reduce[_TypeT]], _TypeT]] = ...,
+    pickle_function: Callable[[_TypeT], str | _Reduce[_TypeT]],
+    constructor_ob: Callable[[_Reduce[_TypeT]], _TypeT] | None = ...,
 ) -> None: ...
 def constructor(object: Callable[[_Reduce[_TypeT]], _TypeT]) -> None: ...
 def add_extension(module: Hashable, name: Hashable, code: SupportsInt) -> None: ...
diff --git a/stdlib/@python2/copyreg.pyi b/stdlib/@python2/copyreg.pyi
index ea07ba410b6d..91b099888bab 100644
--- a/stdlib/@python2/copyreg.pyi
+++ b/stdlib/@python2/copyreg.pyi
@@ -7,8 +7,8 @@ __all__: List[str]
 
 def pickle(
     ob_type: _TypeT,
-    pickle_function: Callable[[_TypeT], Union[str, _Reduce[_TypeT]]],
-    constructor_ob: Optional[Callable[[_Reduce[_TypeT]], _TypeT]] = ...,
+    pickle_function: Callable[[_TypeT], str | _Reduce[_TypeT]],
+    constructor_ob: Callable[[_Reduce[_TypeT]], _TypeT] | None = ...,
 ) -> None: ...
 def constructor(object: Callable[[_Reduce[_TypeT]], _TypeT]) -> None: ...
 def add_extension(module: Hashable, name: Hashable, code: SupportsInt) -> None: ...
diff --git a/stdlib/@python2/csv.pyi b/stdlib/@python2/csv.pyi
index 944c04065ae0..886de6210ca9 100644
--- a/stdlib/@python2/csv.pyi
+++ b/stdlib/@python2/csv.pyi
@@ -24,7 +24,6 @@ from typing import (
     Iterator,
     List,
     Mapping,
-    Optional,
     Sequence,
     Text,
     Type,
@@ -46,9 +45,9 @@ class excel_tab(excel):
     delimiter: str
 
 class DictReader(Generic[_T], Iterator[_DictReadMapping[_T, str]]):
-    fieldnames: Optional[Sequence[_T]]
-    restkey: Optional[str]
-    restval: Optional[str]
+    fieldnames: Sequence[_T] | None
+    restkey: str | None
+    restval: str | None
     reader: _reader
     dialect: _DialectLike
     line_num: int
@@ -57,8 +56,8 @@ class DictReader(Generic[_T], Iterator[_DictReadMapping[_T, str]]):
         self,
         f: Iterable[Text],
         fieldnames: Sequence[_T],
-        restkey: Optional[str] = ...,
-        restval: Optional[str] = ...,
+        restkey: str | None = ...,
+        restval: str | None = ...,
         dialect: _DialectLike = ...,
         *args: Any,
         **kwds: Any,
@@ -67,9 +66,9 @@ class DictReader(Generic[_T], Iterator[_DictReadMapping[_T, str]]):
     def __init__(
         self: DictReader[str],
         f: Iterable[Text],
-        fieldnames: Optional[Sequence[str]] = ...,
-        restkey: Optional[str] = ...,
-        restval: Optional[str] = ...,
+        fieldnames: Sequence[str] | None = ...,
+        restkey: str | None = ...,
+        restval: str | None = ...,
         dialect: _DialectLike = ...,
         *args: Any,
         **kwds: Any,
@@ -79,14 +78,14 @@ class DictReader(Generic[_T], Iterator[_DictReadMapping[_T, str]]):
 
 class DictWriter(Generic[_T]):
     fieldnames: Sequence[_T]
-    restval: Optional[Any]
+    restval: Any | None
     extrasaction: str
     writer: _writer
     def __init__(
         self,
         f: Any,
         fieldnames: Sequence[_T],
-        restval: Optional[Any] = ...,
+        restval: Any | None = ...,
         extrasaction: str = ...,
         dialect: _DialectLike = ...,
         *args: Any,
@@ -99,5 +98,5 @@ class DictWriter(Generic[_T]):
 class Sniffer(object):
     preferred: List[str]
     def __init__(self) -> None: ...
-    def sniff(self, sample: str, delimiters: Optional[str] = ...) -> Type[Dialect]: ...
+    def sniff(self, sample: str, delimiters: str | None = ...) -> Type[Dialect]: ...
     def has_header(self, sample: str) -> bool: ...
diff --git a/stdlib/@python2/ctypes/__init__.pyi b/stdlib/@python2/ctypes/__init__.pyi
index 4adaa3975a82..149e9f281647 100644
--- a/stdlib/@python2/ctypes/__init__.pyi
+++ b/stdlib/@python2/ctypes/__init__.pyi
@@ -34,7 +34,7 @@ class CDLL(object):
     _handle: int = ...
     _FuncPtr: Type[_FuncPointer] = ...
     def __init__(
-        self, name: Optional[str], mode: int = ..., handle: Optional[int] = ..., use_errno: bool = ..., use_last_error: bool = ...
+        self, name: str | None, mode: int = ..., handle: int | None = ..., use_errno: bool = ..., use_last_error: bool = ...
     ) -> None: ...
     def __getattr__(self, name: str) -> _NamedFuncPointer: ...
     def __getitem__(self, name: str) -> _NamedFuncPointer: ...
@@ -75,7 +75,7 @@ class _CDataMeta(type):
 class _CData(metaclass=_CDataMeta):
     _b_base: int = ...
     _b_needsfree_: bool = ...
-    _objects: Optional[Mapping[Any, int]] = ...
+    _objects: Mapping[Any, int] | None = ...
     @classmethod
     def from_buffer(cls: Type[_CT], source: _WritableBuffer, offset: int = ...) -> _CT: ...
     @classmethod
@@ -113,15 +113,15 @@ class _NamedFuncPointer(_FuncPointer):
 class ArgumentError(Exception): ...
 
 def CFUNCTYPE(
-    restype: Optional[Type[_CData]], *argtypes: Type[_CData], use_errno: bool = ..., use_last_error: bool = ...
+    restype: Type[_CData] | None, *argtypes: Type[_CData], use_errno: bool = ..., use_last_error: bool = ...
 ) -> Type[_FuncPointer]: ...
 
 if sys.platform == "win32":
     def WINFUNCTYPE(
-        restype: Optional[Type[_CData]], *argtypes: Type[_CData], use_errno: bool = ..., use_last_error: bool = ...
+        restype: Type[_CData] | None, *argtypes: Type[_CData], use_errno: bool = ..., use_last_error: bool = ...
     ) -> Type[_FuncPointer]: ...
 
-def PYFUNCTYPE(restype: Optional[Type[_CData]], *argtypes: Type[_CData]) -> Type[_FuncPointer]: ...
+def PYFUNCTYPE(restype: Type[_CData] | None, *argtypes: Type[_CData]) -> Type[_FuncPointer]: ...
 
 class _CArgObject: ...
 
@@ -141,11 +141,11 @@ def byref(obj: _CData, offset: int = ...) -> _CArgObject: ...
 _CastT = TypeVar("_CastT", bound=_CanCastTo)
 
 def cast(obj: _UnionT[_CData, _CArgObject, int], typ: Type[_CastT]) -> _CastT: ...
-def create_string_buffer(init: _UnionT[int, bytes], size: Optional[int] = ...) -> Array[c_char]: ...
+def create_string_buffer(init: _UnionT[int, bytes], size: int | None = ...) -> Array[c_char]: ...
 
 c_buffer = create_string_buffer
 
-def create_unicode_buffer(init: _UnionT[int, Text], size: Optional[int] = ...) -> Array[c_wchar]: ...
+def create_unicode_buffer(init: _UnionT[int, Text], size: int | None = ...) -> Array[c_wchar]: ...
 
 if sys.platform == "win32":
     def DllCanUnloadNow() -> int: ...
@@ -189,7 +189,7 @@ def sizeof(obj_or_type: _UnionT[_CData, Type[_CData]]) -> int: ...
 def string_at(address: _CVoidConstPLike, size: int = ...) -> bytes: ...
 
 if sys.platform == "win32":
-    def WinError(code: Optional[int] = ..., descr: Optional[str] = ...) -> OSError: ...
+    def WinError(code: int | None = ..., descr: str | None = ...) -> OSError: ...
 
 def wstring_at(address: _CVoidConstPLike, size: int = ...) -> str: ...
 
@@ -203,7 +203,7 @@ class c_char(_SimpleCData[bytes]):
     def __init__(self, value: _UnionT[int, bytes] = ...) -> None: ...
 
 class c_char_p(_PointerLike, _SimpleCData[Optional[bytes]]):
-    def __init__(self, value: Optional[_UnionT[int, bytes]] = ...) -> None: ...
+    def __init__(self, value: _UnionT[int, bytes] | None = ...) -> None: ...
 
 class c_double(_SimpleCData[float]): ...
 class c_longdouble(_SimpleCData[float]): ...
@@ -231,7 +231,7 @@ class c_void_p(_PointerLike, _SimpleCData[Optional[int]]): ...
 class c_wchar(_SimpleCData[Text]): ...
 
 class c_wchar_p(_PointerLike, _SimpleCData[Optional[Text]]):
-    def __init__(self, value: Optional[_UnionT[int, Text]] = ...) -> None: ...
+    def __init__(self, value: _UnionT[int, Text] | None = ...) -> None: ...
 
 class c_bool(_SimpleCData[bool]):
     def __init__(self, value: bool = ...) -> None: ...
diff --git a/stdlib/@python2/ctypes/util.pyi b/stdlib/@python2/ctypes/util.pyi
index 20914c70a05c..c0274f5e539b 100644
--- a/stdlib/@python2/ctypes/util.pyi
+++ b/stdlib/@python2/ctypes/util.pyi
@@ -1,7 +1,6 @@
 import sys
-from typing import Optional
 
-def find_library(name: str) -> Optional[str]: ...
+def find_library(name: str) -> str | None: ...
 
 if sys.platform == "win32":
-    def find_msvcrt() -> Optional[str]: ...
+    def find_msvcrt() -> str | None: ...
diff --git a/stdlib/@python2/curses/ascii.pyi b/stdlib/@python2/curses/ascii.pyi
index 10bab853adcf..05efb326687a 100644
--- a/stdlib/@python2/curses/ascii.pyi
+++ b/stdlib/@python2/curses/ascii.pyi
@@ -1,4 +1,4 @@
-from typing import List, TypeVar, Union
+from typing import List, TypeVar
 
 _CharT = TypeVar("_CharT", str, int)
 
@@ -41,22 +41,22 @@ DEL: int
 
 controlnames: List[int]
 
-def isalnum(c: Union[str, int]) -> bool: ...
-def isalpha(c: Union[str, int]) -> bool: ...
-def isascii(c: Union[str, int]) -> bool: ...
-def isblank(c: Union[str, int]) -> bool: ...
-def iscntrl(c: Union[str, int]) -> bool: ...
-def isdigit(c: Union[str, int]) -> bool: ...
-def isgraph(c: Union[str, int]) -> bool: ...
-def islower(c: Union[str, int]) -> bool: ...
-def isprint(c: Union[str, int]) -> bool: ...
-def ispunct(c: Union[str, int]) -> bool: ...
-def isspace(c: Union[str, int]) -> bool: ...
-def isupper(c: Union[str, int]) -> bool: ...
-def isxdigit(c: Union[str, int]) -> bool: ...
-def isctrl(c: Union[str, int]) -> bool: ...
-def ismeta(c: Union[str, int]) -> bool: ...
+def isalnum(c: str | int) -> bool: ...
+def isalpha(c: str | int) -> bool: ...
+def isascii(c: str | int) -> bool: ...
+def isblank(c: str | int) -> bool: ...
+def iscntrl(c: str | int) -> bool: ...
+def isdigit(c: str | int) -> bool: ...
+def isgraph(c: str | int) -> bool: ...
+def islower(c: str | int) -> bool: ...
+def isprint(c: str | int) -> bool: ...
+def ispunct(c: str | int) -> bool: ...
+def isspace(c: str | int) -> bool: ...
+def isupper(c: str | int) -> bool: ...
+def isxdigit(c: str | int) -> bool: ...
+def isctrl(c: str | int) -> bool: ...
+def ismeta(c: str | int) -> bool: ...
 def ascii(c: _CharT) -> _CharT: ...
 def ctrl(c: _CharT) -> _CharT: ...
 def alt(c: _CharT) -> _CharT: ...
-def unctrl(c: Union[str, int]) -> str: ...
+def unctrl(c: str | int) -> str: ...
diff --git a/stdlib/@python2/curses/textpad.pyi b/stdlib/@python2/curses/textpad.pyi
index d2b5766fda26..578a579fda38 100644
--- a/stdlib/@python2/curses/textpad.pyi
+++ b/stdlib/@python2/curses/textpad.pyi
@@ -1,11 +1,11 @@
 from _curses import _CursesWindow
-from typing import Callable, Optional, Union
+from typing import Callable
 
 def rectangle(win: _CursesWindow, uly: int, ulx: int, lry: int, lrx: int) -> None: ...
 
 class Textbox:
     stripspaces: bool
     def __init__(self, win: _CursesWindow, insert_mode: bool = ...) -> None: ...
-    def edit(self, validate: Optional[Callable[[int], int]] = ...) -> str: ...
-    def do_command(self, ch: Union[str, int]) -> None: ...
+    def edit(self, validate: Callable[[int], int] | None = ...) -> str: ...
+    def do_command(self, ch: str | int) -> None: ...
     def gather(self) -> str: ...
diff --git a/stdlib/@python2/datetime.pyi b/stdlib/@python2/datetime.pyi
index d1b0d6437825..8b19a3d316f2 100644
--- a/stdlib/@python2/datetime.pyi
+++ b/stdlib/@python2/datetime.pyi
@@ -1,5 +1,5 @@
 from time import struct_time
-from typing import AnyStr, ClassVar, Optional, SupportsAbs, Tuple, Type, TypeVar, Union, overload
+from typing import AnyStr, ClassVar, SupportsAbs, Tuple, Type, TypeVar, Union, overload
 
 _S = TypeVar("_S")
 
@@ -9,9 +9,9 @@ MINYEAR: int
 MAXYEAR: int
 
 class tzinfo:
-    def tzname(self, dt: Optional[datetime]) -> Optional[str]: ...
-    def utcoffset(self, dt: Optional[datetime]) -> Optional[timedelta]: ...
-    def dst(self, dt: Optional[datetime]) -> Optional[timedelta]: ...
+    def tzname(self, dt: datetime | None) -> str | None: ...
+    def utcoffset(self, dt: datetime | None) -> timedelta | None: ...
+    def dst(self, dt: datetime | None) -> timedelta | None: ...
     def fromutc(self, dt: datetime) -> datetime: ...
 
 _tzinfo = tzinfo
@@ -60,12 +60,7 @@ class time:
     max: ClassVar[time]
     resolution: ClassVar[timedelta]
     def __new__(
-        cls: Type[_S],
-        hour: int = ...,
-        minute: int = ...,
-        second: int = ...,
-        microsecond: int = ...,
-        tzinfo: Optional[_tzinfo] = ...,
+        cls: Type[_S], hour: int = ..., minute: int = ..., second: int = ..., microsecond: int = ..., tzinfo: _tzinfo | None = ...
     ) -> _S: ...
     @property
     def hour(self) -> int: ...
@@ -76,7 +71,7 @@ class time:
     @property
     def microsecond(self) -> int: ...
     @property
-    def tzinfo(self) -> Optional[_tzinfo]: ...
+    def tzinfo(self) -> _tzinfo | None: ...
     def __le__(self, other: time) -> bool: ...
     def __lt__(self, other: time) -> bool: ...
     def __ge__(self, other: time) -> bool: ...
@@ -85,11 +80,11 @@ class time:
     def isoformat(self) -> str: ...
     def strftime(self, fmt: _Text) -> str: ...
     def __format__(self, fmt: AnyStr) -> AnyStr: ...
-    def utcoffset(self) -> Optional[timedelta]: ...
-    def tzname(self) -> Optional[str]: ...
-    def dst(self) -> Optional[timedelta]: ...
+    def utcoffset(self) -> timedelta | None: ...
+    def tzname(self) -> str | None: ...
+    def dst(self) -> timedelta | None: ...
     def replace(
-        self, hour: int = ..., minute: int = ..., second: int = ..., microsecond: int = ..., tzinfo: Optional[_tzinfo] = ...
+        self, hour: int = ..., minute: int = ..., second: int = ..., microsecond: int = ..., tzinfo: _tzinfo | None = ...
     ) -> time: ...
 
 _date = date
@@ -152,7 +147,7 @@ class datetime(date):
         minute: int = ...,
         second: int = ...,
         microsecond: int = ...,
-        tzinfo: Optional[_tzinfo] = ...,
+        tzinfo: _tzinfo | None = ...,
     ) -> _S: ...
     @property
     def year(self) -> int: ...
@@ -169,9 +164,9 @@ class datetime(date):
     @property
     def microsecond(self) -> int: ...
     @property
-    def tzinfo(self) -> Optional[_tzinfo]: ...
+    def tzinfo(self) -> _tzinfo | None: ...
     @classmethod
-    def fromtimestamp(cls: Type[_S], t: float, tz: Optional[_tzinfo] = ...) -> _S: ...
+    def fromtimestamp(cls: Type[_S], t: float, tz: _tzinfo | None = ...) -> _S: ...
     @classmethod
     def utcfromtimestamp(cls: Type[_S], t: float) -> _S: ...
     @classmethod
@@ -205,16 +200,16 @@ class datetime(date):
         minute: int = ...,
         second: int = ...,
         microsecond: int = ...,
-        tzinfo: Optional[_tzinfo] = ...,
+        tzinfo: _tzinfo | None = ...,
     ) -> datetime: ...
     def astimezone(self, tz: _tzinfo) -> datetime: ...
     def ctime(self) -> str: ...
     def isoformat(self, sep: str = ...) -> str: ...
     @classmethod
     def strptime(cls, date_string: _Text, format: _Text) -> datetime: ...
-    def utcoffset(self) -> Optional[timedelta]: ...
-    def tzname(self) -> Optional[str]: ...
-    def dst(self) -> Optional[timedelta]: ...
+    def utcoffset(self) -> timedelta | None: ...
+    def tzname(self) -> str | None: ...
+    def dst(self) -> timedelta | None: ...
     def __le__(self, other: datetime) -> bool: ...  # type: ignore
     def __lt__(self, other: datetime) -> bool: ...  # type: ignore
     def __ge__(self, other: datetime) -> bool: ...  # type: ignore
diff --git a/stdlib/@python2/dbm/__init__.pyi b/stdlib/@python2/dbm/__init__.pyi
index edce1ea02861..95f6d9cf0363 100644
--- a/stdlib/@python2/dbm/__init__.pyi
+++ b/stdlib/@python2/dbm/__init__.pyi
@@ -1,5 +1,5 @@
 from types import TracebackType
-from typing import Iterator, MutableMapping, Optional, Tuple, Type, Union
+from typing import Iterator, MutableMapping, Tuple, Type, Union
 from typing_extensions import Literal
 
 _KeyType = Union[str, bytes]
@@ -15,7 +15,7 @@ class _Database(MutableMapping[_KeyType, bytes]):
     def __del__(self) -> None: ...
     def __enter__(self) -> _Database: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
 
 class _error(Exception): ...
diff --git a/stdlib/@python2/dbm/dumb.pyi b/stdlib/@python2/dbm/dumb.pyi
index 0b8ee50a79b7..fb5e2da5fa2c 100644
--- a/stdlib/@python2/dbm/dumb.pyi
+++ b/stdlib/@python2/dbm/dumb.pyi
@@ -1,5 +1,5 @@
 from types import TracebackType
-from typing import Iterator, MutableMapping, Optional, Type, Union
+from typing import Iterator, MutableMapping, Type, Union
 
 _KeyType = Union[str, bytes]
 _ValueType = Union[str, bytes]
@@ -19,7 +19,7 @@ class _Database(MutableMapping[_KeyType, bytes]):
     def __del__(self) -> None: ...
     def __enter__(self) -> _Database: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
 
 def open(file: str, flag: str = ..., mode: int = ...) -> _Database: ...
diff --git a/stdlib/@python2/dbm/gnu.pyi b/stdlib/@python2/dbm/gnu.pyi
index 8f13a2988488..0e9339bf81f9 100644
--- a/stdlib/@python2/dbm/gnu.pyi
+++ b/stdlib/@python2/dbm/gnu.pyi
@@ -1,5 +1,5 @@
 from types import TracebackType
-from typing import List, Optional, Type, TypeVar, Union, overload
+from typing import List, Type, TypeVar, Union, overload
 
 _T = TypeVar("_T")
 _KeyType = Union[str, bytes]
@@ -9,8 +9,8 @@ class error(OSError): ...
 
 # Actual typename gdbm, not exposed by the implementation
 class _gdbm:
-    def firstkey(self) -> Optional[bytes]: ...
-    def nextkey(self, key: _KeyType) -> Optional[bytes]: ...
+    def firstkey(self) -> bytes | None: ...
+    def nextkey(self, key: _KeyType) -> bytes | None: ...
     def reorganize(self) -> None: ...
     def sync(self) -> None: ...
     def close(self) -> None: ...
@@ -20,12 +20,12 @@ class _gdbm:
     def __len__(self) -> int: ...
     def __enter__(self) -> _gdbm: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
     @overload
-    def get(self, k: _KeyType) -> Optional[bytes]: ...
+    def get(self, k: _KeyType) -> bytes | None: ...
     @overload
-    def get(self, k: _KeyType, default: Union[bytes, _T]) -> Union[bytes, _T]: ...
+    def get(self, k: _KeyType, default: bytes | _T) -> bytes | _T: ...
     def keys(self) -> List[bytes]: ...
     def setdefault(self, k: _KeyType, default: _ValueType = ...) -> bytes: ...
     # Don't exist at runtime
diff --git a/stdlib/@python2/dbm/ndbm.pyi b/stdlib/@python2/dbm/ndbm.pyi
index 020131543e13..28f4dd8e4e59 100644
--- a/stdlib/@python2/dbm/ndbm.pyi
+++ b/stdlib/@python2/dbm/ndbm.pyi
@@ -1,5 +1,5 @@
 from types import TracebackType
-from typing import List, Optional, Type, TypeVar, Union, overload
+from typing import List, Type, TypeVar, Union, overload
 
 _T = TypeVar("_T")
 _KeyType = Union[str, bytes]
@@ -19,12 +19,12 @@ class _dbm:
     def __del__(self) -> None: ...
     def __enter__(self) -> _dbm: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
     @overload
-    def get(self, k: _KeyType) -> Optional[bytes]: ...
+    def get(self, k: _KeyType) -> bytes | None: ...
     @overload
-    def get(self, k: _KeyType, default: Union[bytes, _T]) -> Union[bytes, _T]: ...
+    def get(self, k: _KeyType, default: bytes | _T) -> bytes | _T: ...
     def keys(self) -> List[bytes]: ...
     def setdefault(self, k: _KeyType, default: _ValueType = ...) -> bytes: ...
     # Don't exist at runtime
diff --git a/stdlib/@python2/decimal.pyi b/stdlib/@python2/decimal.pyi
index bee33d9c7af0..915bddadb584 100644
--- a/stdlib/@python2/decimal.pyi
+++ b/stdlib/@python2/decimal.pyi
@@ -1,5 +1,5 @@
 from types import TracebackType
-from typing import Any, Container, Dict, List, NamedTuple, Optional, Sequence, Text, Tuple, Type, TypeVar, Union
+from typing import Any, Container, Dict, List, NamedTuple, Sequence, Text, Tuple, Type, TypeVar, Union
 
 _Decimal = Union[Decimal, int]
 _DecimalNew = Union[Decimal, float, Text, Tuple[int, Sequence[int], int]]
@@ -21,7 +21,7 @@ ROUND_HALF_DOWN: str
 ROUND_05UP: str
 
 class DecimalException(ArithmeticError):
-    def handle(self, context: Context, *args: Any) -> Optional[Decimal]: ...
+    def handle(self, context: Context, *args: Any) -> Decimal | None: ...
 
 class Clamped(DecimalException): ...
 class InvalidOperation(DecimalException): ...
@@ -38,45 +38,45 @@ class Underflow(Inexact, Rounded, Subnormal): ...
 
 def setcontext(__context: Context) -> None: ...
 def getcontext() -> Context: ...
-def localcontext(ctx: Optional[Context] = ...) -> _ContextManager: ...
+def localcontext(ctx: Context | None = ...) -> _ContextManager: ...
 
 class Decimal(object):
-    def __new__(cls: Type[_DecimalT], value: _DecimalNew = ..., context: Optional[Context] = ...) -> _DecimalT: ...
+    def __new__(cls: Type[_DecimalT], value: _DecimalNew = ..., context: Context | None = ...) -> _DecimalT: ...
     @classmethod
     def from_float(cls, __f: float) -> Decimal: ...
     def __nonzero__(self) -> bool: ...
-    def __div__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __rdiv__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __ne__(self, other: object, context: Optional[Context] = ...) -> bool: ...
-    def compare(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
+    def __div__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __rdiv__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __ne__(self, other: object, context: Context | None = ...) -> bool: ...
+    def compare(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
     def __hash__(self) -> int: ...
     def as_tuple(self) -> DecimalTuple: ...
-    def to_eng_string(self, context: Optional[Context] = ...) -> str: ...
-    def __abs__(self, round: bool = ..., context: Optional[Context] = ...) -> Decimal: ...
-    def __add__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __divmod__(self, other: _Decimal, context: Optional[Context] = ...) -> Tuple[Decimal, Decimal]: ...
-    def __eq__(self, other: object, context: Optional[Context] = ...) -> bool: ...
-    def __floordiv__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __ge__(self, other: _ComparableNum, context: Optional[Context] = ...) -> bool: ...
-    def __gt__(self, other: _ComparableNum, context: Optional[Context] = ...) -> bool: ...
-    def __le__(self, other: _ComparableNum, context: Optional[Context] = ...) -> bool: ...
-    def __lt__(self, other: _ComparableNum, context: Optional[Context] = ...) -> bool: ...
-    def __mod__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __mul__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __neg__(self, context: Optional[Context] = ...) -> Decimal: ...
-    def __pos__(self, context: Optional[Context] = ...) -> Decimal: ...
-    def __pow__(self, other: _Decimal, modulo: Optional[_Decimal] = ..., context: Optional[Context] = ...) -> Decimal: ...
-    def __radd__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __rdivmod__(self, other: _Decimal, context: Optional[Context] = ...) -> Tuple[Decimal, Decimal]: ...
-    def __rfloordiv__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __rmod__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __rmul__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __rsub__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __rtruediv__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __str__(self, eng: bool = ..., context: Optional[Context] = ...) -> str: ...
-    def __sub__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __truediv__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def remainder_near(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
+    def to_eng_string(self, context: Context | None = ...) -> str: ...
+    def __abs__(self, round: bool = ..., context: Context | None = ...) -> Decimal: ...
+    def __add__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __divmod__(self, other: _Decimal, context: Context | None = ...) -> Tuple[Decimal, Decimal]: ...
+    def __eq__(self, other: object, context: Context | None = ...) -> bool: ...
+    def __floordiv__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __ge__(self, other: _ComparableNum, context: Context | None = ...) -> bool: ...
+    def __gt__(self, other: _ComparableNum, context: Context | None = ...) -> bool: ...
+    def __le__(self, other: _ComparableNum, context: Context | None = ...) -> bool: ...
+    def __lt__(self, other: _ComparableNum, context: Context | None = ...) -> bool: ...
+    def __mod__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __mul__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __neg__(self, context: Context | None = ...) -> Decimal: ...
+    def __pos__(self, context: Context | None = ...) -> Decimal: ...
+    def __pow__(self, other: _Decimal, modulo: _Decimal | None = ..., context: Context | None = ...) -> Decimal: ...
+    def __radd__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __rdivmod__(self, other: _Decimal, context: Context | None = ...) -> Tuple[Decimal, Decimal]: ...
+    def __rfloordiv__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __rmod__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __rmul__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __rsub__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __rtruediv__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __str__(self, eng: bool = ..., context: Context | None = ...) -> str: ...
+    def __sub__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __truediv__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def remainder_near(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
     def __float__(self) -> float: ...
     def __int__(self) -> int: ...
     def __trunc__(self) -> int: ...
@@ -87,66 +87,66 @@ class Decimal(object):
     def conjugate(self) -> Decimal: ...
     def __complex__(self) -> complex: ...
     def __long__(self) -> long: ...
-    def fma(self, other: _Decimal, third: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def __rpow__(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def normalize(self, context: Optional[Context] = ...) -> Decimal: ...
+    def fma(self, other: _Decimal, third: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def __rpow__(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def normalize(self, context: Context | None = ...) -> Decimal: ...
     def quantize(
-        self, exp: _Decimal, rounding: Optional[str] = ..., context: Optional[Context] = ..., watchexp: bool = ...
+        self, exp: _Decimal, rounding: str | None = ..., context: Context | None = ..., watchexp: bool = ...
     ) -> Decimal: ...
     def same_quantum(self, other: _Decimal) -> bool: ...
-    def to_integral_exact(self, rounding: Optional[str] = ..., context: Optional[Context] = ...) -> Decimal: ...
-    def to_integral_value(self, rounding: Optional[str] = ..., context: Optional[Context] = ...) -> Decimal: ...
-    def to_integral(self, rounding: Optional[str] = ..., context: Optional[Context] = ...) -> Decimal: ...
-    def sqrt(self, context: Optional[Context] = ...) -> Decimal: ...
-    def max(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def min(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
+    def to_integral_exact(self, rounding: str | None = ..., context: Context | None = ...) -> Decimal: ...
+    def to_integral_value(self, rounding: str | None = ..., context: Context | None = ...) -> Decimal: ...
+    def to_integral(self, rounding: str | None = ..., context: Context | None = ...) -> Decimal: ...
+    def sqrt(self, context: Context | None = ...) -> Decimal: ...
+    def max(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def min(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
     def adjusted(self) -> int: ...
-    def canonical(self, context: Optional[Context] = ...) -> Decimal: ...
-    def compare_signal(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
+    def canonical(self, context: Context | None = ...) -> Decimal: ...
+    def compare_signal(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
     def compare_total(self, other: _Decimal) -> Decimal: ...
     def compare_total_mag(self, other: _Decimal) -> Decimal: ...
     def copy_abs(self) -> Decimal: ...
     def copy_negate(self) -> Decimal: ...
     def copy_sign(self, other: _Decimal) -> Decimal: ...
-    def exp(self, context: Optional[Context] = ...) -> Decimal: ...
+    def exp(self, context: Context | None = ...) -> Decimal: ...
     def is_canonical(self) -> bool: ...
     def is_finite(self) -> bool: ...
     def is_infinite(self) -> bool: ...
     def is_nan(self) -> bool: ...
-    def is_normal(self, context: Optional[Context] = ...) -> bool: ...
+    def is_normal(self, context: Context | None = ...) -> bool: ...
     def is_qnan(self) -> bool: ...
     def is_signed(self) -> bool: ...
     def is_snan(self) -> bool: ...
-    def is_subnormal(self, context: Optional[Context] = ...) -> bool: ...
+    def is_subnormal(self, context: Context | None = ...) -> bool: ...
     def is_zero(self) -> bool: ...
-    def ln(self, context: Optional[Context] = ...) -> Decimal: ...
-    def log10(self, context: Optional[Context] = ...) -> Decimal: ...
-    def logb(self, context: Optional[Context] = ...) -> Decimal: ...
-    def logical_and(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def logical_invert(self, context: Optional[Context] = ...) -> Decimal: ...
-    def logical_or(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def logical_xor(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def max_mag(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def min_mag(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def next_minus(self, context: Optional[Context] = ...) -> Decimal: ...
-    def next_plus(self, context: Optional[Context] = ...) -> Decimal: ...
-    def next_toward(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def number_class(self, context: Optional[Context] = ...) -> str: ...
+    def ln(self, context: Context | None = ...) -> Decimal: ...
+    def log10(self, context: Context | None = ...) -> Decimal: ...
+    def logb(self, context: Context | None = ...) -> Decimal: ...
+    def logical_and(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def logical_invert(self, context: Context | None = ...) -> Decimal: ...
+    def logical_or(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def logical_xor(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def max_mag(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def min_mag(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def next_minus(self, context: Context | None = ...) -> Decimal: ...
+    def next_plus(self, context: Context | None = ...) -> Decimal: ...
+    def next_toward(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def number_class(self, context: Context | None = ...) -> str: ...
     def radix(self) -> Decimal: ...
-    def rotate(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def scaleb(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
-    def shift(self, other: _Decimal, context: Optional[Context] = ...) -> Decimal: ...
+    def rotate(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def scaleb(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
+    def shift(self, other: _Decimal, context: Context | None = ...) -> Decimal: ...
     def __reduce__(self) -> Tuple[Type[Decimal], Tuple[str]]: ...
     def __copy__(self) -> Decimal: ...
     def __deepcopy__(self, memo: Any) -> Decimal: ...
-    def __format__(self, specifier: str, context: Optional[Context] = ...) -> str: ...
+    def __format__(self, specifier: str, context: Context | None = ...) -> str: ...
 
 class _ContextManager(object):
     new_context: Context
     saved_context: Context
     def __init__(self, new_context: Context) -> None: ...
     def __enter__(self) -> Context: ...
-    def __exit__(self, t: Optional[Type[BaseException]], v: Optional[BaseException], tb: Optional[TracebackType]) -> None: ...
+    def __exit__(self, t: Type[BaseException] | None, v: BaseException | None, tb: TracebackType | None) -> None: ...
 
 _TrapType = Type[DecimalException]
 
@@ -161,15 +161,15 @@ class Context(object):
     flags: Dict[_TrapType, bool]
     def __init__(
         self,
-        prec: Optional[int] = ...,
-        rounding: Optional[str] = ...,
-        traps: Union[None, Dict[_TrapType, bool], Container[_TrapType]] = ...,
-        flags: Union[None, Dict[_TrapType, bool], Container[_TrapType]] = ...,
-        Emin: Optional[int] = ...,
-        Emax: Optional[int] = ...,
-        capitals: Optional[int] = ...,
-        _clamp: Optional[int] = ...,
-        _ignored_flags: Optional[List[_TrapType]] = ...,
+        prec: int | None = ...,
+        rounding: str | None = ...,
+        traps: None | Dict[_TrapType, bool] | Container[_TrapType] = ...,
+        flags: None | Dict[_TrapType, bool] | Container[_TrapType] = ...,
+        Emin: int | None = ...,
+        Emax: int | None = ...,
+        capitals: int | None = ...,
+        _clamp: int | None = ...,
+        _ignored_flags: List[_TrapType] | None = ...,
     ) -> None: ...
     def clear_flags(self) -> None: ...
     def copy(self) -> Context: ...
@@ -224,7 +224,7 @@ class Context(object):
     def normalize(self, __x: _Decimal) -> Decimal: ...
     def number_class(self, __x: _Decimal) -> str: ...
     def plus(self, __x: _Decimal) -> Decimal: ...
-    def power(self, a: _Decimal, b: _Decimal, modulo: Optional[_Decimal] = ...) -> Decimal: ...
+    def power(self, a: _Decimal, b: _Decimal, modulo: _Decimal | None = ...) -> Decimal: ...
     def quantize(self, __x: _Decimal, __y: _Decimal) -> Decimal: ...
     def radix(self) -> Decimal: ...
     def remainder(self, __x: _Decimal, __y: _Decimal) -> Decimal: ...
diff --git a/stdlib/@python2/difflib.pyi b/stdlib/@python2/difflib.pyi
index 02dbbb64433c..41ffc6a286d1 100644
--- a/stdlib/@python2/difflib.pyi
+++ b/stdlib/@python2/difflib.pyi
@@ -7,7 +7,6 @@ from typing import (
     Iterator,
     List,
     NamedTuple,
-    Optional,
     Sequence,
     Text,
     Tuple,
@@ -30,7 +29,7 @@ class Match(NamedTuple):
 
 class SequenceMatcher(Generic[_T]):
     def __init__(
-        self, isjunk: Optional[Callable[[_T], bool]] = ..., a: Sequence[_T] = ..., b: Sequence[_T] = ..., autojunk: bool = ...
+        self, isjunk: Callable[[_T], bool] | None = ..., a: Sequence[_T] = ..., b: Sequence[_T] = ..., autojunk: bool = ...
     ) -> None: ...
     def set_seqs(self, a: Sequence[_T], b: Sequence[_T]) -> None: ...
     def set_seq1(self, a: Sequence[_T]) -> None: ...
@@ -54,7 +53,7 @@ def get_close_matches(
 ) -> List[Sequence[_T]]: ...
 
 class Differ:
-    def __init__(self, linejunk: Optional[_JunkCallback] = ..., charjunk: Optional[_JunkCallback] = ...) -> None: ...
+    def __init__(self, linejunk: _JunkCallback | None = ..., charjunk: _JunkCallback | None = ...) -> None: ...
     def compare(self, a: Sequence[_StrType], b: Sequence[_StrType]) -> Iterator[_StrType]: ...
 
 def IS_LINE_JUNK(line: _StrType, pat: Any = ...) -> bool: ...  # pat is undocumented
@@ -80,16 +79,16 @@ def context_diff(
     lineterm: _StrType = ...,
 ) -> Iterator[_StrType]: ...
 def ndiff(
-    a: Sequence[_StrType], b: Sequence[_StrType], linejunk: Optional[_JunkCallback] = ..., charjunk: Optional[_JunkCallback] = ...
+    a: Sequence[_StrType], b: Sequence[_StrType], linejunk: _JunkCallback | None = ..., charjunk: _JunkCallback | None = ...
 ) -> Iterator[_StrType]: ...
 
 class HtmlDiff(object):
     def __init__(
         self,
         tabsize: int = ...,
-        wrapcolumn: Optional[int] = ...,
-        linejunk: Optional[_JunkCallback] = ...,
-        charjunk: Optional[_JunkCallback] = ...,
+        wrapcolumn: int | None = ...,
+        linejunk: _JunkCallback | None = ...,
+        charjunk: _JunkCallback | None = ...,
     ) -> None: ...
     def make_file(
         self,
diff --git a/stdlib/@python2/dircache.pyi b/stdlib/@python2/dircache.pyi
index fd906f6f2ae1..366909d87133 100644
--- a/stdlib/@python2/dircache.pyi
+++ b/stdlib/@python2/dircache.pyi
@@ -1,8 +1,8 @@
-from typing import List, MutableSequence, Text, Union
+from typing import List, MutableSequence, Text
 
 def reset() -> None: ...
 def listdir(path: Text) -> List[str]: ...
 
 opendir = listdir
 
-def annotate(head: Text, list: Union[MutableSequence[str], MutableSequence[Text], MutableSequence[Union[str, Text]]]) -> None: ...
+def annotate(head: Text, list: MutableSequence[str] | MutableSequence[Text] | MutableSequence[str | Text]) -> None: ...
diff --git a/stdlib/@python2/distutils/archive_util.pyi b/stdlib/@python2/distutils/archive_util.pyi
index 0e94d3818ae4..dd2cbda73fc6 100644
--- a/stdlib/@python2/distutils/archive_util.pyi
+++ b/stdlib/@python2/distutils/archive_util.pyi
@@ -1,12 +1,5 @@
-from typing import Optional
-
 def make_archive(
-    base_name: str,
-    format: str,
-    root_dir: Optional[str] = ...,
-    base_dir: Optional[str] = ...,
-    verbose: int = ...,
-    dry_run: int = ...,
+    base_name: str, format: str, root_dir: str | None = ..., base_dir: str | None = ..., verbose: int = ..., dry_run: int = ...
 ) -> str: ...
-def make_tarball(base_name: str, base_dir: str, compress: Optional[str] = ..., verbose: int = ..., dry_run: int = ...) -> str: ...
+def make_tarball(base_name: str, base_dir: str, compress: str | None = ..., verbose: int = ..., dry_run: int = ...) -> str: ...
 def make_zipfile(base_name: str, base_dir: str, verbose: int = ..., dry_run: int = ...) -> str: ...
diff --git a/stdlib/@python2/distutils/ccompiler.pyi b/stdlib/@python2/distutils/ccompiler.pyi
index 831311d2cb52..b0539bf9e5dc 100644
--- a/stdlib/@python2/distutils/ccompiler.pyi
+++ b/stdlib/@python2/distutils/ccompiler.pyi
@@ -6,9 +6,9 @@ def gen_lib_options(
     compiler: CCompiler, library_dirs: List[str], runtime_library_dirs: List[str], libraries: List[str]
 ) -> List[str]: ...
 def gen_preprocess_options(macros: List[_Macro], include_dirs: List[str]) -> List[str]: ...
-def get_default_compiler(osname: Optional[str] = ..., platform: Optional[str] = ...) -> str: ...
+def get_default_compiler(osname: str | None = ..., platform: str | None = ...) -> str: ...
 def new_compiler(
-    plat: Optional[str] = ..., compiler: Optional[str] = ..., verbose: int = ..., dry_run: int = ..., force: int = ...
+    plat: str | None = ..., compiler: str | None = ..., verbose: int = ..., dry_run: int = ..., force: int = ...
 ) -> CCompiler: ...
 def show_compilers() -> None: ...
 
@@ -16,7 +16,7 @@ class CCompiler:
     dry_run: bool
     force: bool
     verbose: bool
-    output_dir: Optional[str]
+    output_dir: str | None
     macros: List[_Macro]
     include_dirs: List[str]
     libraries: List[str]
@@ -32,19 +32,19 @@ class CCompiler:
     def set_library_dirs(self, dirs: List[str]) -> None: ...
     def add_runtime_library_dir(self, dir: str) -> None: ...
     def set_runtime_library_dirs(self, dirs: List[str]) -> None: ...
-    def define_macro(self, name: str, value: Optional[str] = ...) -> None: ...
+    def define_macro(self, name: str, value: str | None = ...) -> None: ...
     def undefine_macro(self, name: str) -> None: ...
     def add_link_object(self, object: str) -> None: ...
     def set_link_objects(self, objects: List[str]) -> None: ...
-    def detect_language(self, sources: Union[str, List[str]]) -> Optional[str]: ...
-    def find_library_file(self, dirs: List[str], lib: str, debug: bool = ...) -> Optional[str]: ...
+    def detect_language(self, sources: str | List[str]) -> str | None: ...
+    def find_library_file(self, dirs: List[str], lib: str, debug: bool = ...) -> str | None: ...
     def has_function(
         self,
         funcname: str,
-        includes: Optional[List[str]] = ...,
-        include_dirs: Optional[List[str]] = ...,
-        libraries: Optional[List[str]] = ...,
-        library_dirs: Optional[List[str]] = ...,
+        includes: List[str] | None = ...,
+        include_dirs: List[str] | None = ...,
+        libraries: List[str] | None = ...,
+        library_dirs: List[str] | None = ...,
     ) -> bool: ...
     def library_dir_option(self, dir: str) -> str: ...
     def library_option(self, lib: str) -> str: ...
@@ -53,95 +53,95 @@ class CCompiler:
     def compile(
         self,
         sources: List[str],
-        output_dir: Optional[str] = ...,
-        macros: Optional[_Macro] = ...,
-        include_dirs: Optional[List[str]] = ...,
+        output_dir: str | None = ...,
+        macros: _Macro | None = ...,
+        include_dirs: List[str] | None = ...,
         debug: bool = ...,
-        extra_preargs: Optional[List[str]] = ...,
-        extra_postargs: Optional[List[str]] = ...,
-        depends: Optional[List[str]] = ...,
+        extra_preargs: List[str] | None = ...,
+        extra_postargs: List[str] | None = ...,
+        depends: List[str] | None = ...,
     ) -> List[str]: ...
     def create_static_lib(
         self,
         objects: List[str],
         output_libname: str,
-        output_dir: Optional[str] = ...,
+        output_dir: str | None = ...,
         debug: bool = ...,
-        target_lang: Optional[str] = ...,
+        target_lang: str | None = ...,
     ) -> None: ...
     def link(
         self,
         target_desc: str,
         objects: List[str],
         output_filename: str,
-        output_dir: Optional[str] = ...,
-        libraries: Optional[List[str]] = ...,
-        library_dirs: Optional[List[str]] = ...,
-        runtime_library_dirs: Optional[List[str]] = ...,
-        export_symbols: Optional[List[str]] = ...,
+        output_dir: str | None = ...,
+        libraries: List[str] | None = ...,
+        library_dirs: List[str] | None = ...,
+        runtime_library_dirs: List[str] | None = ...,
+        export_symbols: List[str] | None = ...,
         debug: bool = ...,
-        extra_preargs: Optional[List[str]] = ...,
-        extra_postargs: Optional[List[str]] = ...,
-        build_temp: Optional[str] = ...,
-        target_lang: Optional[str] = ...,
+        extra_preargs: List[str] | None = ...,
+        extra_postargs: List[str] | None = ...,
+        build_temp: str | None = ...,
+        target_lang: str | None = ...,
     ) -> None: ...
     def link_executable(
         self,
         objects: List[str],
         output_progname: str,
-        output_dir: Optional[str] = ...,
-        libraries: Optional[List[str]] = ...,
-        library_dirs: Optional[List[str]] = ...,
-        runtime_library_dirs: Optional[List[str]] = ...,
+        output_dir: str | None = ...,
+        libraries: List[str] | None = ...,
+        library_dirs: List[str] | None = ...,
+        runtime_library_dirs: List[str] | None = ...,
         debug: bool = ...,
-        extra_preargs: Optional[List[str]] = ...,
-        extra_postargs: Optional[List[str]] = ...,
-        target_lang: Optional[str] = ...,
+        extra_preargs: List[str] | None = ...,
+        extra_postargs: List[str] | None = ...,
+        target_lang: str | None = ...,
     ) -> None: ...
     def link_shared_lib(
         self,
         objects: List[str],
         output_libname: str,
-        output_dir: Optional[str] = ...,
-        libraries: Optional[List[str]] = ...,
-        library_dirs: Optional[List[str]] = ...,
-        runtime_library_dirs: Optional[List[str]] = ...,
-        export_symbols: Optional[List[str]] = ...,
+        output_dir: str | None = ...,
+        libraries: List[str] | None = ...,
+        library_dirs: List[str] | None = ...,
+        runtime_library_dirs: List[str] | None = ...,
+        export_symbols: List[str] | None = ...,
         debug: bool = ...,
-        extra_preargs: Optional[List[str]] = ...,
-        extra_postargs: Optional[List[str]] = ...,
-        build_temp: Optional[str] = ...,
-        target_lang: Optional[str] = ...,
+        extra_preargs: List[str] | None = ...,
+        extra_postargs: List[str] | None = ...,
+        build_temp: str | None = ...,
+        target_lang: str | None = ...,
     ) -> None: ...
     def link_shared_object(
         self,
         objects: List[str],
         output_filename: str,
-        output_dir: Optional[str] = ...,
-        libraries: Optional[List[str]] = ...,
-        library_dirs: Optional[List[str]] = ...,
-        runtime_library_dirs: Optional[List[str]] = ...,
-        export_symbols: Optional[List[str]] = ...,
+        output_dir: str | None = ...,
+        libraries: List[str] | None = ...,
+        library_dirs: List[str] | None = ...,
+        runtime_library_dirs: List[str] | None = ...,
+        export_symbols: List[str] | None = ...,
         debug: bool = ...,
-        extra_preargs: Optional[List[str]] = ...,
-        extra_postargs: Optional[List[str]] = ...,
-        build_temp: Optional[str] = ...,
-        target_lang: Optional[str] = ...,
+        extra_preargs: List[str] | None = ...,
+        extra_postargs: List[str] | None = ...,
+        build_temp: str | None = ...,
+        target_lang: str | None = ...,
     ) -> None: ...
     def preprocess(
         self,
         source: str,
-        output_file: Optional[str] = ...,
-        macros: Optional[List[_Macro]] = ...,
-        include_dirs: Optional[List[str]] = ...,
-        extra_preargs: Optional[List[str]] = ...,
-        extra_postargs: Optional[List[str]] = ...,
+        output_file: str | None = ...,
+        macros: List[_Macro] | None = ...,
+        include_dirs: List[str] | None = ...,
+        extra_preargs: List[str] | None = ...,
+        extra_postargs: List[str] | None = ...,
     ) -> None: ...
     def executable_filename(self, basename: str, strip_dir: int = ..., output_dir: str = ...) -> str: ...
     def library_filename(self, libname: str, lib_type: str = ..., strip_dir: int = ..., output_dir: str = ...) -> str: ...
     def object_filenames(self, source_filenames: List[str], strip_dir: int = ..., output_dir: str = ...) -> List[str]: ...
     def shared_object_filename(self, basename: str, strip_dir: int = ..., output_dir: str = ...) -> str: ...
-    def execute(self, func: Callable[..., None], args: Tuple[Any, ...], msg: Optional[str] = ..., level: int = ...) -> None: ...
+    def execute(self, func: Callable[..., None], args: Tuple[Any, ...], msg: str | None = ..., level: int = ...) -> None: ...
     def spawn(self, cmd: List[str]) -> None: ...
     def mkpath(self, name: str, mode: int = ...) -> None: ...
     def move_file(self, src: str, dst: str) -> str: ...
diff --git a/stdlib/@python2/distutils/cmd.pyi b/stdlib/@python2/distutils/cmd.pyi
index b888c189f932..d4e90bf69970 100644
--- a/stdlib/@python2/distutils/cmd.pyi
+++ b/stdlib/@python2/distutils/cmd.pyi
@@ -1,9 +1,9 @@
 from abc import abstractmethod
 from distutils.dist import Distribution
-from typing import Any, Callable, Iterable, List, Optional, Text, Tuple, Union
+from typing import Any, Callable, Iterable, List, Text, Tuple
 
 class Command:
-    sub_commands: List[Tuple[str, Optional[Callable[[Command], bool]]]]
+    sub_commands: List[Tuple[str, Callable[[Command], bool] | None]]
     def __init__(self, dist: Distribution) -> None: ...
     @abstractmethod
     def initialize_options(self) -> None: ...
@@ -13,18 +13,18 @@ class Command:
     def run(self) -> None: ...
     def announce(self, msg: Text, level: int = ...) -> None: ...
     def debug_print(self, msg: Text) -> None: ...
-    def ensure_string(self, option: str, default: Optional[str] = ...) -> None: ...
-    def ensure_string_list(self, option: Union[str, List[str]]) -> None: ...
+    def ensure_string(self, option: str, default: str | None = ...) -> None: ...
+    def ensure_string_list(self, option: str | List[str]) -> None: ...
     def ensure_filename(self, option: str) -> None: ...
     def ensure_dirname(self, option: str) -> None: ...
     def get_command_name(self) -> str: ...
     def set_undefined_options(self, src_cmd: Text, *option_pairs: Tuple[str, str]) -> None: ...
     def get_finalized_command(self, command: Text, create: int = ...) -> Command: ...
-    def reinitialize_command(self, command: Union[Command, Text], reinit_subcommands: int = ...) -> Command: ...
+    def reinitialize_command(self, command: Command | Text, reinit_subcommands: int = ...) -> Command: ...
     def run_command(self, command: Text) -> None: ...
     def get_sub_commands(self) -> List[str]: ...
     def warn(self, msg: Text) -> None: ...
-    def execute(self, func: Callable[..., Any], args: Iterable[Any], msg: Optional[Text] = ..., level: int = ...) -> None: ...
+    def execute(self, func: Callable[..., Any], args: Iterable[Any], msg: Text | None = ..., level: int = ...) -> None: ...
     def mkpath(self, name: str, mode: int = ...) -> None: ...
     def copy_file(
         self,
@@ -32,7 +32,7 @@ class Command:
         outfile: str,
         preserve_mode: int = ...,
         preserve_times: int = ...,
-        link: Optional[str] = ...,
+        link: str | None = ...,
         level: Any = ...,
     ) -> Tuple[str, bool]: ...  # level is not used
     def copy_tree(
@@ -50,18 +50,18 @@ class Command:
         self,
         base_name: str,
         format: str,
-        root_dir: Optional[str] = ...,
-        base_dir: Optional[str] = ...,
-        owner: Optional[str] = ...,
-        group: Optional[str] = ...,
+        root_dir: str | None = ...,
+        base_dir: str | None = ...,
+        owner: str | None = ...,
+        group: str | None = ...,
     ) -> str: ...
     def make_file(
         self,
-        infiles: Union[str, List[str], Tuple[str]],
+        infiles: str | List[str] | Tuple[str],
         outfile: str,
         func: Callable[..., Any],
         args: List[Any],
-        exec_msg: Optional[str] = ...,
-        skip_msg: Optional[str] = ...,
+        exec_msg: str | None = ...,
+        skip_msg: str | None = ...,
         level: Any = ...,
     ) -> None: ...  # level is not used
diff --git a/stdlib/@python2/distutils/command/config.pyi b/stdlib/@python2/distutils/command/config.pyi
index 6b57a64b48b1..d0fd762e83b2 100644
--- a/stdlib/@python2/distutils/command/config.pyi
+++ b/stdlib/@python2/distutils/command/config.pyi
@@ -3,19 +3,19 @@ from distutils.ccompiler import CCompiler
 from distutils.core import Command as Command
 from distutils.errors import DistutilsExecError as DistutilsExecError
 from distutils.sysconfig import customize_compiler as customize_compiler
-from typing import Dict, List, Optional, Pattern, Sequence, Tuple, Union
+from typing import Dict, List, Pattern, Sequence, Tuple
 
 LANG_EXT: Dict[str, str]
 
 class config(Command):
     description: str = ...
     # Tuple is full name, short name, description
-    user_options: Sequence[Tuple[str, Optional[str], str]] = ...
-    compiler: Optional[Union[str, CCompiler]] = ...
-    cc: Optional[str] = ...
-    include_dirs: Optional[Sequence[str]] = ...
-    libraries: Optional[Sequence[str]] = ...
-    library_dirs: Optional[Sequence[str]] = ...
+    user_options: Sequence[Tuple[str, str | None, str]] = ...
+    compiler: str | CCompiler | None = ...
+    cc: str | None = ...
+    include_dirs: Sequence[str] | None = ...
+    libraries: Sequence[str] | None = ...
+    library_dirs: Sequence[str] | None = ...
     noisy: int = ...
     dump_source: int = ...
     temp_files: Sequence[str] = ...
@@ -24,64 +24,60 @@ class config(Command):
     def run(self) -> None: ...
     def try_cpp(
         self,
-        body: Optional[str] = ...,
-        headers: Optional[Sequence[str]] = ...,
-        include_dirs: Optional[Sequence[str]] = ...,
+        body: str | None = ...,
+        headers: Sequence[str] | None = ...,
+        include_dirs: Sequence[str] | None = ...,
         lang: str = ...,
     ) -> bool: ...
     def search_cpp(
         self,
-        pattern: Union[Pattern[str], str],
-        body: Optional[str] = ...,
-        headers: Optional[Sequence[str]] = ...,
-        include_dirs: Optional[Sequence[str]] = ...,
+        pattern: Pattern[str] | str,
+        body: str | None = ...,
+        headers: Sequence[str] | None = ...,
+        include_dirs: Sequence[str] | None = ...,
         lang: str = ...,
     ) -> bool: ...
     def try_compile(
-        self, body: str, headers: Optional[Sequence[str]] = ..., include_dirs: Optional[Sequence[str]] = ..., lang: str = ...
+        self, body: str, headers: Sequence[str] | None = ..., include_dirs: Sequence[str] | None = ..., lang: str = ...
     ) -> bool: ...
     def try_link(
         self,
         body: str,
-        headers: Optional[Sequence[str]] = ...,
-        include_dirs: Optional[Sequence[str]] = ...,
-        libraries: Optional[Sequence[str]] = ...,
-        library_dirs: Optional[Sequence[str]] = ...,
+        headers: Sequence[str] | None = ...,
+        include_dirs: Sequence[str] | None = ...,
+        libraries: Sequence[str] | None = ...,
+        library_dirs: Sequence[str] | None = ...,
         lang: str = ...,
     ) -> bool: ...
     def try_run(
         self,
         body: str,
-        headers: Optional[Sequence[str]] = ...,
-        include_dirs: Optional[Sequence[str]] = ...,
-        libraries: Optional[Sequence[str]] = ...,
-        library_dirs: Optional[Sequence[str]] = ...,
+        headers: Sequence[str] | None = ...,
+        include_dirs: Sequence[str] | None = ...,
+        libraries: Sequence[str] | None = ...,
+        library_dirs: Sequence[str] | None = ...,
         lang: str = ...,
     ) -> bool: ...
     def check_func(
         self,
         func: str,
-        headers: Optional[Sequence[str]] = ...,
-        include_dirs: Optional[Sequence[str]] = ...,
-        libraries: Optional[Sequence[str]] = ...,
-        library_dirs: Optional[Sequence[str]] = ...,
+        headers: Sequence[str] | None = ...,
+        include_dirs: Sequence[str] | None = ...,
+        libraries: Sequence[str] | None = ...,
+        library_dirs: Sequence[str] | None = ...,
         decl: int = ...,
         call: int = ...,
     ) -> bool: ...
     def check_lib(
         self,
         library: str,
-        library_dirs: Optional[Sequence[str]] = ...,
-        headers: Optional[Sequence[str]] = ...,
-        include_dirs: Optional[Sequence[str]] = ...,
+        library_dirs: Sequence[str] | None = ...,
+        headers: Sequence[str] | None = ...,
+        include_dirs: Sequence[str] | None = ...,
         other_libraries: List[str] = ...,
     ) -> bool: ...
     def check_header(
-        self,
-        header: str,
-        include_dirs: Optional[Sequence[str]] = ...,
-        library_dirs: Optional[Sequence[str]] = ...,
-        lang: str = ...,
+        self, header: str, include_dirs: Sequence[str] | None = ..., library_dirs: Sequence[str] | None = ..., lang: str = ...
     ) -> bool: ...
 
-def dump_file(filename: str, head: Optional[str] = ...) -> None: ...
+def dump_file(filename: str, head: str | None = ...) -> None: ...
diff --git a/stdlib/@python2/distutils/command/install.pyi b/stdlib/@python2/distutils/command/install.pyi
index dc6d96b82a62..2824236735f0 100644
--- a/stdlib/@python2/distutils/command/install.pyi
+++ b/stdlib/@python2/distutils/command/install.pyi
@@ -1,12 +1,12 @@
 from distutils.cmd import Command
-from typing import Optional, Text
+from typing import Text
 
 class install(Command):
     user: bool
-    prefix: Optional[Text]
-    home: Optional[Text]
-    root: Optional[Text]
-    install_lib: Optional[Text]
+    prefix: Text | None
+    home: Text | None
+    root: Text | None
+    install_lib: Text | None
     def initialize_options(self) -> None: ...
     def finalize_options(self) -> None: ...
     def run(self) -> None: ...
diff --git a/stdlib/@python2/distutils/command/install_egg_info.pyi b/stdlib/@python2/distutils/command/install_egg_info.pyi
index 80ffb19bda74..bf3d0737f244 100644
--- a/stdlib/@python2/distutils/command/install_egg_info.pyi
+++ b/stdlib/@python2/distutils/command/install_egg_info.pyi
@@ -1,9 +1,9 @@
 from distutils.cmd import Command
-from typing import ClassVar, List, Optional, Tuple
+from typing import ClassVar, List, Tuple
 
 class install_egg_info(Command):
     description: ClassVar[str]
-    user_options: ClassVar[List[Tuple[str, Optional[str], str]]]
+    user_options: ClassVar[List[Tuple[str, str | None, str]]]
     def initialize_options(self) -> None: ...
     def finalize_options(self) -> None: ...
     def run(self) -> None: ...
diff --git a/stdlib/@python2/distutils/command/upload.pyi b/stdlib/@python2/distutils/command/upload.pyi
index c49a4e5b4937..3835d9fd6ec6 100644
--- a/stdlib/@python2/distutils/command/upload.pyi
+++ b/stdlib/@python2/distutils/command/upload.pyi
@@ -1,5 +1,5 @@
 from distutils.config import PyPIRCCommand
-from typing import ClassVar, List, Optional, Tuple
+from typing import ClassVar, List, Tuple
 
 class upload(PyPIRCCommand):
     description: ClassVar[str]
diff --git a/stdlib/@python2/distutils/config.pyi b/stdlib/@python2/distutils/config.pyi
index e60507e0b65a..bcd626c81d48 100644
--- a/stdlib/@python2/distutils/config.pyi
+++ b/stdlib/@python2/distutils/config.pyi
@@ -1,6 +1,6 @@
 from abc import abstractmethod
 from distutils.cmd import Command
-from typing import ClassVar, List, Optional, Tuple
+from typing import ClassVar, List, Tuple
 
 DEFAULT_PYPIRC: str
 
@@ -9,7 +9,7 @@ class PyPIRCCommand(Command):
     DEFAULT_REALM: ClassVar[str]
     repository: None
     realm: None
-    user_options: ClassVar[List[Tuple[str, Optional[str], str]]]
+    user_options: ClassVar[List[Tuple[str, str | None, str]]]
     boolean_options: ClassVar[List[str]]
     def initialize_options(self) -> None: ...
     def finalize_options(self) -> None: ...
diff --git a/stdlib/@python2/distutils/core.pyi b/stdlib/@python2/distutils/core.pyi
index 9a3fa70fd381..48bd7b5018bc 100644
--- a/stdlib/@python2/distutils/core.pyi
+++ b/stdlib/@python2/distutils/core.pyi
@@ -1,7 +1,7 @@
 from distutils.cmd import Command as Command
 from distutils.dist import Distribution as Distribution
 from distutils.extension import Extension as Extension
-from typing import Any, List, Mapping, Optional, Tuple, Type, Union
+from typing import Any, List, Mapping, Tuple, Type
 
 def setup(
     *,
@@ -25,8 +25,8 @@ def setup(
     script_args: List[str] = ...,
     options: Mapping[str, Any] = ...,
     license: str = ...,
-    keywords: Union[List[str], str] = ...,
-    platforms: Union[List[str], str] = ...,
+    keywords: List[str] | str = ...,
+    platforms: List[str] | str = ...,
     cmdclass: Mapping[str, Type[Command]] = ...,
     data_files: List[Tuple[str, List[str]]] = ...,
     package_dir: Mapping[str, str] = ...,
@@ -45,4 +45,4 @@ def setup(
     fullname: str = ...,
     **attrs: Any,
 ) -> None: ...
-def run_setup(script_name: str, script_args: Optional[List[str]] = ..., stop_after: str = ...) -> Distribution: ...
+def run_setup(script_name: str, script_args: List[str] | None = ..., stop_after: str = ...) -> Distribution: ...
diff --git a/stdlib/@python2/distutils/dist.pyi b/stdlib/@python2/distutils/dist.pyi
index 685423bda6da..adba8f093569 100644
--- a/stdlib/@python2/distutils/dist.pyi
+++ b/stdlib/@python2/distutils/dist.pyi
@@ -1,9 +1,9 @@
 from distutils.cmd import Command
-from typing import Any, Dict, Iterable, Mapping, Optional, Text, Tuple, Type
+from typing import Any, Dict, Iterable, Mapping, Text, Tuple, Type
 
 class Distribution:
     cmdclass: Dict[str, Type[Command]]
-    def __init__(self, attrs: Optional[Mapping[str, Any]] = ...) -> None: ...
+    def __init__(self, attrs: Mapping[str, Any] | None = ...) -> None: ...
     def get_option_dict(self, command: str) -> Dict[str, Tuple[str, Text]]: ...
-    def parse_config_files(self, filenames: Optional[Iterable[Text]] = ...) -> None: ...
-    def get_command_obj(self, command: str, create: bool = ...) -> Optional[Command]: ...
+    def parse_config_files(self, filenames: Iterable[Text] | None = ...) -> None: ...
+    def get_command_obj(self, command: str, create: bool = ...) -> Command | None: ...
diff --git a/stdlib/@python2/distutils/extension.pyi b/stdlib/@python2/distutils/extension.pyi
index 02c1f55617b3..9335fad86418 100644
--- a/stdlib/@python2/distutils/extension.pyi
+++ b/stdlib/@python2/distutils/extension.pyi
@@ -1,4 +1,4 @@
-from typing import List, Optional, Tuple
+from typing import List, Tuple
 
 class Extension:
     def __init__(
@@ -6,7 +6,7 @@ class Extension:
         name: str,
         sources: List[str],
         include_dirs: List[str] = ...,
-        define_macros: List[Tuple[str, Optional[str]]] = ...,
+        define_macros: List[Tuple[str, str | None]] = ...,
         undef_macros: List[str] = ...,
         library_dirs: List[str] = ...,
         libraries: List[str] = ...,
@@ -15,7 +15,7 @@ class Extension:
         extra_compile_args: List[str] = ...,
         extra_link_args: List[str] = ...,
         export_symbols: List[str] = ...,
-        swig_opts: Optional[str] = ...,  # undocumented
+        swig_opts: str | None = ...,  # undocumented
         depends: List[str] = ...,
         language: str = ...,
     ) -> None: ...
diff --git a/stdlib/@python2/distutils/fancy_getopt.pyi b/stdlib/@python2/distutils/fancy_getopt.pyi
index 8eb4c416fa28..d0e3309c2d77 100644
--- a/stdlib/@python2/distutils/fancy_getopt.pyi
+++ b/stdlib/@python2/distutils/fancy_getopt.pyi
@@ -1,21 +1,21 @@
-from typing import Any, List, Mapping, Optional, Tuple, Union, overload
+from typing import Any, List, Mapping, Optional, Tuple, overload
 
 _Option = Tuple[str, Optional[str], str]
 _GR = Tuple[List[str], OptionDummy]
 
 def fancy_getopt(
-    options: List[_Option], negative_opt: Mapping[_Option, _Option], object: Any, args: Optional[List[str]]
-) -> Union[List[str], _GR]: ...
+    options: List[_Option], negative_opt: Mapping[_Option, _Option], object: Any, args: List[str] | None
+) -> List[str] | _GR: ...
 def wrap_text(text: str, width: int) -> List[str]: ...
 
 class FancyGetopt:
-    def __init__(self, option_table: Optional[List[_Option]] = ...) -> None: ...
+    def __init__(self, option_table: List[_Option] | None = ...) -> None: ...
     # TODO kinda wrong, `getopt(object=object())` is invalid
     @overload
-    def getopt(self, args: Optional[List[str]] = ...) -> _GR: ...
+    def getopt(self, args: List[str] | None = ...) -> _GR: ...
     @overload
-    def getopt(self, args: Optional[List[str]], object: Any) -> List[str]: ...
+    def getopt(self, args: List[str] | None, object: Any) -> List[str]: ...
     def get_option_order(self) -> List[Tuple[str, str]]: ...
-    def generate_help(self, header: Optional[str] = ...) -> List[str]: ...
+    def generate_help(self, header: str | None = ...) -> List[str]: ...
 
 class OptionDummy: ...
diff --git a/stdlib/@python2/distutils/file_util.pyi b/stdlib/@python2/distutils/file_util.pyi
index 018339733df0..cfe840e71040 100644
--- a/stdlib/@python2/distutils/file_util.pyi
+++ b/stdlib/@python2/distutils/file_util.pyi
@@ -1,4 +1,4 @@
-from typing import Optional, Sequence, Tuple
+from typing import Sequence, Tuple
 
 def copy_file(
     src: str,
@@ -6,7 +6,7 @@ def copy_file(
     preserve_mode: bool = ...,
     preserve_times: bool = ...,
     update: bool = ...,
-    link: Optional[str] = ...,
+    link: str | None = ...,
     verbose: bool = ...,
     dry_run: bool = ...,
 ) -> Tuple[str, str]: ...
diff --git a/stdlib/@python2/distutils/spawn.pyi b/stdlib/@python2/distutils/spawn.pyi
index e12eae99bf29..0fffc5402c62 100644
--- a/stdlib/@python2/distutils/spawn.pyi
+++ b/stdlib/@python2/distutils/spawn.pyi
@@ -1,4 +1,4 @@
-from typing import List, Optional
+from typing import List
 
 def spawn(cmd: List[str], search_path: bool = ..., verbose: bool = ..., dry_run: bool = ...) -> None: ...
-def find_executable(executable: str, path: Optional[str] = ...) -> Optional[str]: ...
+def find_executable(executable: str, path: str | None = ...) -> str | None: ...
diff --git a/stdlib/@python2/distutils/sysconfig.pyi b/stdlib/@python2/distutils/sysconfig.pyi
index 9061db75ccf1..7d9fe7d34de3 100644
--- a/stdlib/@python2/distutils/sysconfig.pyi
+++ b/stdlib/@python2/distutils/sysconfig.pyi
@@ -1,14 +1,14 @@
 from distutils.ccompiler import CCompiler
-from typing import Mapping, Optional, Union
+from typing import Mapping
 
 PREFIX: str
 EXEC_PREFIX: str
 
-def get_config_var(name: str) -> Union[int, str, None]: ...
-def get_config_vars(*args: str) -> Mapping[str, Union[int, str]]: ...
+def get_config_var(name: str) -> int | str | None: ...
+def get_config_vars(*args: str) -> Mapping[str, int | str]: ...
 def get_config_h_filename() -> str: ...
 def get_makefile_filename() -> str: ...
-def get_python_inc(plat_specific: bool = ..., prefix: Optional[str] = ...) -> str: ...
-def get_python_lib(plat_specific: bool = ..., standard_lib: bool = ..., prefix: Optional[str] = ...) -> str: ...
+def get_python_inc(plat_specific: bool = ..., prefix: str | None = ...) -> str: ...
+def get_python_lib(plat_specific: bool = ..., standard_lib: bool = ..., prefix: str | None = ...) -> str: ...
 def customize_compiler(compiler: CCompiler) -> None: ...
 def set_python_build() -> None: ...
diff --git a/stdlib/@python2/distutils/text_file.pyi b/stdlib/@python2/distutils/text_file.pyi
index 9872a1f25751..26ba5a6fabb6 100644
--- a/stdlib/@python2/distutils/text_file.pyi
+++ b/stdlib/@python2/distutils/text_file.pyi
@@ -1,10 +1,10 @@
-from typing import IO, List, Optional, Tuple, Union
+from typing import IO, List, Tuple
 
 class TextFile:
     def __init__(
         self,
-        filename: Optional[str] = ...,
-        file: Optional[IO[str]] = ...,
+        filename: str | None = ...,
+        file: IO[str] | None = ...,
         *,
         strip_comments: bool = ...,
         lstrip_ws: bool = ...,
@@ -15,7 +15,7 @@ class TextFile:
     ) -> None: ...
     def open(self, filename: str) -> None: ...
     def close(self) -> None: ...
-    def warn(self, msg: str, line: Union[List[int], Tuple[int, int], int] = ...) -> None: ...
-    def readline(self) -> Optional[str]: ...
+    def warn(self, msg: str, line: List[int] | Tuple[int, int] | int = ...) -> None: ...
+    def readline(self) -> str | None: ...
     def readlines(self) -> List[str]: ...
     def unreadline(self, line: str) -> str: ...
diff --git a/stdlib/@python2/distutils/util.pyi b/stdlib/@python2/distutils/util.pyi
index 0086d726af65..c0882d1dd1cb 100644
--- a/stdlib/@python2/distutils/util.pyi
+++ b/stdlib/@python2/distutils/util.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, List, Mapping, Optional, Tuple
+from typing import Any, Callable, List, Mapping, Tuple
 
 def get_platform() -> str: ...
 def convert_path(pathname: str) -> str: ...
@@ -7,17 +7,17 @@ def check_environ() -> None: ...
 def subst_vars(s: str, local_vars: Mapping[str, str]) -> None: ...
 def split_quoted(s: str) -> List[str]: ...
 def execute(
-    func: Callable[..., None], args: Tuple[Any, ...], msg: Optional[str] = ..., verbose: bool = ..., dry_run: bool = ...
+    func: Callable[..., None], args: Tuple[Any, ...], msg: str | None = ..., verbose: bool = ..., dry_run: bool = ...
 ) -> None: ...
 def strtobool(val: str) -> bool: ...
 def byte_compile(
     py_files: List[str],
     optimize: int = ...,
     force: bool = ...,
-    prefix: Optional[str] = ...,
-    base_dir: Optional[str] = ...,
+    prefix: str | None = ...,
+    base_dir: str | None = ...,
     verbose: bool = ...,
     dry_run: bool = ...,
-    direct: Optional[bool] = ...,
+    direct: bool | None = ...,
 ) -> None: ...
 def rfc822_escape(header: str) -> str: ...
diff --git a/stdlib/@python2/distutils/version.pyi b/stdlib/@python2/distutils/version.pyi
index f55d01d1a172..dd0969b8635f 100644
--- a/stdlib/@python2/distutils/version.pyi
+++ b/stdlib/@python2/distutils/version.pyi
@@ -1,33 +1,33 @@
 from abc import abstractmethod
-from typing import Optional, Pattern, Text, Tuple, TypeVar, Union
+from typing import Pattern, Text, Tuple, TypeVar
 
 _T = TypeVar("_T", bound=Version)
 
 class Version:
     def __repr__(self) -> str: ...
     @abstractmethod
-    def __init__(self, vstring: Optional[Text] = ...) -> None: ...
+    def __init__(self, vstring: Text | None = ...) -> None: ...
     @abstractmethod
     def parse(self: _T, vstring: Text) -> _T: ...
     @abstractmethod
     def __str__(self) -> str: ...
     @abstractmethod
-    def __cmp__(self: _T, other: Union[_T, str]) -> bool: ...
+    def __cmp__(self: _T, other: _T | str) -> bool: ...
 
 class StrictVersion(Version):
     version_re: Pattern[str]
     version: Tuple[int, int, int]
-    prerelease: Optional[Tuple[Text, int]]
-    def __init__(self, vstring: Optional[Text] = ...) -> None: ...
+    prerelease: Tuple[Text, int] | None
+    def __init__(self, vstring: Text | None = ...) -> None: ...
     def parse(self: _T, vstring: Text) -> _T: ...
     def __str__(self) -> str: ...
-    def __cmp__(self: _T, other: Union[_T, str]) -> bool: ...
+    def __cmp__(self: _T, other: _T | str) -> bool: ...
 
 class LooseVersion(Version):
     component_re: Pattern[str]
     vstring: Text
-    version: Tuple[Union[Text, int], ...]
-    def __init__(self, vstring: Optional[Text] = ...) -> None: ...
+    version: Tuple[Text | int, ...]
+    def __init__(self, vstring: Text | None = ...) -> None: ...
     def parse(self: _T, vstring: Text) -> _T: ...
     def __str__(self) -> str: ...
-    def __cmp__(self: _T, other: Union[_T, str]) -> bool: ...
+    def __cmp__(self: _T, other: _T | str) -> bool: ...
diff --git a/stdlib/@python2/doctest.pyi b/stdlib/@python2/doctest.pyi
index b9e0ab392374..6c3b922244f4 100644
--- a/stdlib/@python2/doctest.pyi
+++ b/stdlib/@python2/doctest.pyi
@@ -1,6 +1,6 @@
 import types
 import unittest
-from typing import Any, Callable, Dict, List, NamedTuple, Optional, Tuple, Type, Union
+from typing import Any, Callable, Dict, List, NamedTuple, Tuple, Type
 
 class TestResults(NamedTuple):
     failed: int
@@ -31,7 +31,7 @@ ELLIPSIS_MARKER: str
 class Example:
     source: str
     want: str
-    exc_msg: Optional[str]
+    exc_msg: str | None
     lineno: int
     indent: int
     options: Dict[int, bool]
@@ -39,10 +39,10 @@ class Example:
         self,
         source: str,
         want: str,
-        exc_msg: Optional[str] = ...,
+        exc_msg: str | None = ...,
         lineno: int = ...,
         indent: int = ...,
-        options: Optional[Dict[int, bool]] = ...,
+        options: Dict[int, bool] | None = ...,
     ) -> None: ...
     def __hash__(self) -> int: ...
 
@@ -50,26 +50,24 @@ class DocTest:
     examples: List[Example]
     globs: Dict[str, Any]
     name: str
-    filename: Optional[str]
-    lineno: Optional[int]
-    docstring: Optional[str]
+    filename: str | None
+    lineno: int | None
+    docstring: str | None
     def __init__(
         self,
         examples: List[Example],
         globs: Dict[str, Any],
         name: str,
-        filename: Optional[str],
-        lineno: Optional[int],
-        docstring: Optional[str],
+        filename: str | None,
+        lineno: int | None,
+        docstring: str | None,
     ) -> None: ...
     def __hash__(self) -> int: ...
     def __lt__(self, other: DocTest) -> bool: ...
 
 class DocTestParser:
-    def parse(self, string: str, name: str = ...) -> List[Union[str, Example]]: ...
-    def get_doctest(
-        self, string: str, globs: Dict[str, Any], name: str, filename: Optional[str], lineno: Optional[int]
-    ) -> DocTest: ...
+    def parse(self, string: str, name: str = ...) -> List[str | Example]: ...
+    def get_doctest(self, string: str, globs: Dict[str, Any], name: str, filename: str | None, lineno: int | None) -> DocTest: ...
     def get_examples(self, string: str, name: str = ...) -> List[Example]: ...
 
 class DocTestFinder:
@@ -79,10 +77,10 @@ class DocTestFinder:
     def find(
         self,
         obj: object,
-        name: Optional[str] = ...,
-        module: Union[None, bool, types.ModuleType] = ...,
-        globs: Optional[Dict[str, Any]] = ...,
-        extraglobs: Optional[Dict[str, Any]] = ...,
+        name: str | None = ...,
+        module: None | bool | types.ModuleType = ...,
+        globs: Dict[str, Any] | None = ...,
+        extraglobs: Dict[str, Any] | None = ...,
     ) -> List[DocTest]: ...
 
 _Out = Callable[[str], Any]
@@ -95,15 +93,15 @@ class DocTestRunner:
     tries: int
     failures: int
     test: DocTest
-    def __init__(self, checker: Optional[OutputChecker] = ..., verbose: Optional[bool] = ..., optionflags: int = ...) -> None: ...
+    def __init__(self, checker: OutputChecker | None = ..., verbose: bool | None = ..., optionflags: int = ...) -> None: ...
     def report_start(self, out: _Out, test: DocTest, example: Example) -> None: ...
     def report_success(self, out: _Out, test: DocTest, example: Example, got: str) -> None: ...
     def report_failure(self, out: _Out, test: DocTest, example: Example, got: str) -> None: ...
     def report_unexpected_exception(self, out: _Out, test: DocTest, example: Example, exc_info: _ExcInfo) -> None: ...
     def run(
-        self, test: DocTest, compileflags: Optional[int] = ..., out: Optional[_Out] = ..., clear_globs: bool = ...
+        self, test: DocTest, compileflags: int | None = ..., out: _Out | None = ..., clear_globs: bool = ...
     ) -> TestResults: ...
-    def summarize(self, verbose: Optional[bool] = ...) -> TestResults: ...
+    def summarize(self, verbose: bool | None = ...) -> TestResults: ...
     def merge(self, other: DocTestRunner) -> None: ...
 
 class OutputChecker:
@@ -124,40 +122,35 @@ class UnexpectedException(Exception):
 
 class DebugRunner(DocTestRunner): ...
 
-master: Optional[DocTestRunner]
+master: DocTestRunner | None
 
 def testmod(
-    m: Optional[types.ModuleType] = ...,
-    name: Optional[str] = ...,
-    globs: Optional[Dict[str, Any]] = ...,
-    verbose: Optional[bool] = ...,
+    m: types.ModuleType | None = ...,
+    name: str | None = ...,
+    globs: Dict[str, Any] | None = ...,
+    verbose: bool | None = ...,
     report: bool = ...,
     optionflags: int = ...,
-    extraglobs: Optional[Dict[str, Any]] = ...,
+    extraglobs: Dict[str, Any] | None = ...,
     raise_on_error: bool = ...,
     exclude_empty: bool = ...,
 ) -> TestResults: ...
 def testfile(
     filename: str,
     module_relative: bool = ...,
-    name: Optional[str] = ...,
-    package: Union[None, str, types.ModuleType] = ...,
-    globs: Optional[Dict[str, Any]] = ...,
-    verbose: Optional[bool] = ...,
+    name: str | None = ...,
+    package: None | str | types.ModuleType = ...,
+    globs: Dict[str, Any] | None = ...,
+    verbose: bool | None = ...,
     report: bool = ...,
     optionflags: int = ...,
-    extraglobs: Optional[Dict[str, Any]] = ...,
+    extraglobs: Dict[str, Any] | None = ...,
     raise_on_error: bool = ...,
     parser: DocTestParser = ...,
-    encoding: Optional[str] = ...,
+    encoding: str | None = ...,
 ) -> TestResults: ...
 def run_docstring_examples(
-    f: object,
-    globs: Dict[str, Any],
-    verbose: bool = ...,
-    name: str = ...,
-    compileflags: Optional[int] = ...,
-    optionflags: int = ...,
+    f: object, globs: Dict[str, Any], verbose: bool = ..., name: str = ..., compileflags: int | None = ..., optionflags: int = ...
 ) -> None: ...
 def set_unittest_reportflags(flags: int) -> int: ...
 
@@ -166,9 +159,9 @@ class DocTestCase(unittest.TestCase):
         self,
         test: DocTest,
         optionflags: int = ...,
-        setUp: Optional[Callable[[DocTest], Any]] = ...,
-        tearDown: Optional[Callable[[DocTest], Any]] = ...,
-        checker: Optional[OutputChecker] = ...,
+        setUp: Callable[[DocTest], Any] | None = ...,
+        tearDown: Callable[[DocTest], Any] | None = ...,
+        checker: OutputChecker | None = ...,
     ) -> None: ...
     def setUp(self) -> None: ...
     def tearDown(self) -> None: ...
@@ -188,10 +181,10 @@ class SkipDocTestCase(DocTestCase):
 _DocTestSuite = unittest.TestSuite
 
 def DocTestSuite(
-    module: Union[None, str, types.ModuleType] = ...,
-    globs: Optional[Dict[str, Any]] = ...,
-    extraglobs: Optional[Dict[str, Any]] = ...,
-    test_finder: Optional[DocTestFinder] = ...,
+    module: None | str | types.ModuleType = ...,
+    globs: Dict[str, Any] | None = ...,
+    extraglobs: Dict[str, Any] | None = ...,
+    test_finder: DocTestFinder | None = ...,
     **options: Any,
 ) -> _DocTestSuite: ...
 
@@ -202,15 +195,15 @@ class DocFileCase(DocTestCase):
 def DocFileTest(
     path: str,
     module_relative: bool = ...,
-    package: Union[None, str, types.ModuleType] = ...,
-    globs: Optional[Dict[str, Any]] = ...,
+    package: None | str | types.ModuleType = ...,
+    globs: Dict[str, Any] | None = ...,
     parser: DocTestParser = ...,
-    encoding: Optional[str] = ...,
+    encoding: str | None = ...,
     **options: Any,
 ) -> DocFileCase: ...
 def DocFileSuite(*paths: str, **kw: Any) -> _DocTestSuite: ...
 def script_from_examples(s: str) -> str: ...
-def testsource(module: Union[None, str, types.ModuleType], name: str) -> str: ...
-def debug_src(src: str, pm: bool = ..., globs: Optional[Dict[str, Any]] = ...) -> None: ...
-def debug_script(src: str, pm: bool = ..., globs: Optional[Dict[str, Any]] = ...) -> None: ...
-def debug(module: Union[None, str, types.ModuleType], name: str, pm: bool = ...) -> None: ...
+def testsource(module: None | str | types.ModuleType, name: str) -> str: ...
+def debug_src(src: str, pm: bool = ..., globs: Dict[str, Any] | None = ...) -> None: ...
+def debug_script(src: str, pm: bool = ..., globs: Dict[str, Any] | None = ...) -> None: ...
+def debug(module: None | str | types.ModuleType, name: str, pm: bool = ...) -> None: ...
diff --git a/stdlib/@python2/dummy_thread.pyi b/stdlib/@python2/dummy_thread.pyi
index 28041002a708..0a28b3aaeeb9 100644
--- a/stdlib/@python2/dummy_thread.pyi
+++ b/stdlib/@python2/dummy_thread.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, Dict, NoReturn, Optional, Tuple
+from typing import Any, Callable, Dict, NoReturn, Tuple
 
 class error(Exception):
     def __init__(self, *args: Any) -> None: ...
@@ -7,13 +7,13 @@ def start_new_thread(function: Callable[..., Any], args: Tuple[Any, ...], kwargs
 def exit() -> NoReturn: ...
 def get_ident() -> int: ...
 def allocate_lock() -> LockType: ...
-def stack_size(size: Optional[int] = ...) -> int: ...
+def stack_size(size: int | None = ...) -> int: ...
 
 class LockType(object):
     locked_status: bool
     def __init__(self) -> None: ...
-    def acquire(self, waitflag: Optional[bool] = ...) -> bool: ...
-    def __enter__(self, waitflag: Optional[bool] = ...) -> bool: ...
+    def acquire(self, waitflag: bool | None = ...) -> bool: ...
+    def __enter__(self, waitflag: bool | None = ...) -> bool: ...
     def __exit__(self, typ: Any, val: Any, tb: Any) -> None: ...
     def release(self) -> bool: ...
     def locked(self) -> bool: ...
diff --git a/stdlib/@python2/email/_parseaddr.pyi b/stdlib/@python2/email/_parseaddr.pyi
index 424ade705f77..74ea3a6e4a69 100644
--- a/stdlib/@python2/email/_parseaddr.pyi
+++ b/stdlib/@python2/email/_parseaddr.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Optional
+from typing import Any
 
 def parsedate_tz(data): ...
 def parsedate(data): ...
@@ -26,7 +26,7 @@ class AddrlistClass:
     def getquote(self): ...
     def getcomment(self): ...
     def getdomainliteral(self): ...
-    def getatom(self, atomends: Optional[Any] = ...): ...
+    def getatom(self, atomends: Any | None = ...): ...
     def getphraselist(self): ...
 
 class AddressList(AddrlistClass):
diff --git a/stdlib/@python2/email/utils.pyi b/stdlib/@python2/email/utils.pyi
index 257e4b1c947a..0d185134c9d7 100644
--- a/stdlib/@python2/email/utils.pyi
+++ b/stdlib/@python2/email/utils.pyi
@@ -5,17 +5,17 @@ from email._parseaddr import (
     parsedate_tz as _parsedate_tz,
 )
 from quopri import decodestring as _qdecode
-from typing import Any, Optional
+from typing import Any
 
 def formataddr(pair): ...
 def getaddresses(fieldvalues): ...
-def formatdate(timeval: Optional[Any] = ..., localtime: bool = ..., usegmt: bool = ...): ...
-def make_msgid(idstring: Optional[Any] = ...): ...
+def formatdate(timeval: Any | None = ..., localtime: bool = ..., usegmt: bool = ...): ...
+def make_msgid(idstring: Any | None = ...): ...
 def parsedate(data): ...
 def parsedate_tz(data): ...
 def parseaddr(addr): ...
 def unquote(str): ...
 def decode_rfc2231(s): ...
-def encode_rfc2231(s, charset: Optional[Any] = ..., language: Optional[Any] = ...): ...
+def encode_rfc2231(s, charset: Any | None = ..., language: Any | None = ...): ...
 def decode_params(params): ...
 def collapse_rfc2231_value(value, errors=..., fallback_charset=...): ...
diff --git a/stdlib/@python2/ensurepip/__init__.pyi b/stdlib/@python2/ensurepip/__init__.pyi
index 8a22ef546436..60946e7cf35a 100644
--- a/stdlib/@python2/ensurepip/__init__.pyi
+++ b/stdlib/@python2/ensurepip/__init__.pyi
@@ -1,8 +1,6 @@
-from typing import Optional
-
 def version() -> str: ...
 def bootstrap(
-    root: Optional[str] = ...,
+    root: str | None = ...,
     upgrade: bool = ...,
     user: bool = ...,
     altinstall: bool = ...,
diff --git a/stdlib/@python2/fcntl.pyi b/stdlib/@python2/fcntl.pyi
index 200e2249280c..b3730270f1cc 100644
--- a/stdlib/@python2/fcntl.pyi
+++ b/stdlib/@python2/fcntl.pyi
@@ -1,5 +1,5 @@
 from _typeshed import FileDescriptorLike
-from typing import Any, Union
+from typing import Any
 
 FASYNC: int
 FD_CLOEXEC: int
@@ -74,9 +74,9 @@ LOCK_WRITE: int
 
 # TODO All these return either int or bytes depending on the value of
 # cmd (not on the type of arg).
-def fcntl(fd: FileDescriptorLike, op: int, arg: Union[int, bytes] = ...) -> Any: ...
+def fcntl(fd: FileDescriptorLike, op: int, arg: int | bytes = ...) -> Any: ...
 
 # TODO: arg: int or read-only buffer interface or read-write buffer interface
-def ioctl(fd: FileDescriptorLike, op: int, arg: Union[int, bytes] = ..., mutate_flag: bool = ...) -> Any: ...
+def ioctl(fd: FileDescriptorLike, op: int, arg: int | bytes = ..., mutate_flag: bool = ...) -> Any: ...
 def flock(fd: FileDescriptorLike, op: int) -> None: ...
 def lockf(fd: FileDescriptorLike, op: int, length: int = ..., start: int = ..., whence: int = ...) -> Any: ...
diff --git a/stdlib/@python2/filecmp.pyi b/stdlib/@python2/filecmp.pyi
index 73fe39580c55..0be5596c2bdb 100644
--- a/stdlib/@python2/filecmp.pyi
+++ b/stdlib/@python2/filecmp.pyi
@@ -1,15 +1,15 @@
-from typing import AnyStr, Callable, Dict, Generic, Iterable, List, Optional, Sequence, Text, Tuple, Union
+from typing import AnyStr, Callable, Dict, Generic, Iterable, List, Sequence, Text, Tuple
 
 DEFAULT_IGNORES: List[str]
 
-def cmp(f1: Union[bytes, Text], f2: Union[bytes, Text], shallow: Union[int, bool] = ...) -> bool: ...
+def cmp(f1: bytes | Text, f2: bytes | Text, shallow: int | bool = ...) -> bool: ...
 def cmpfiles(
-    a: AnyStr, b: AnyStr, common: Iterable[AnyStr], shallow: Union[int, bool] = ...
+    a: AnyStr, b: AnyStr, common: Iterable[AnyStr], shallow: int | bool = ...
 ) -> Tuple[List[AnyStr], List[AnyStr], List[AnyStr]]: ...
 
 class dircmp(Generic[AnyStr]):
     def __init__(
-        self, a: AnyStr, b: AnyStr, ignore: Optional[Sequence[AnyStr]] = ..., hide: Optional[Sequence[AnyStr]] = ...
+        self, a: AnyStr, b: AnyStr, ignore: Sequence[AnyStr] | None = ..., hide: Sequence[AnyStr] | None = ...
     ) -> None: ...
     left: AnyStr
     right: AnyStr
diff --git a/stdlib/@python2/fileinput.pyi b/stdlib/@python2/fileinput.pyi
index 1e1f8dace600..316643fcf15f 100644
--- a/stdlib/@python2/fileinput.pyi
+++ b/stdlib/@python2/fileinput.pyi
@@ -1,7 +1,7 @@
-from typing import IO, Any, AnyStr, Callable, Generic, Iterable, Iterator, Text, Union
+from typing import IO, Any, AnyStr, Callable, Generic, Iterable, Iterator, Text
 
 def input(
-    files: Union[Text, Iterable[Text], None] = ...,
+    files: Text | Iterable[Text] | None = ...,
     inplace: bool = ...,
     backup: str = ...,
     bufsize: int = ...,
@@ -20,7 +20,7 @@ def isstdin() -> bool: ...
 class FileInput(Iterable[AnyStr], Generic[AnyStr]):
     def __init__(
         self,
-        files: Union[None, Text, Iterable[Text]] = ...,
+        files: None | Text | Iterable[Text] = ...,
         inplace: bool = ...,
         backup: str = ...,
         bufsize: int = ...,
diff --git a/stdlib/@python2/formatter.pyi b/stdlib/@python2/formatter.pyi
index 31c45592a215..da165f2d55e3 100644
--- a/stdlib/@python2/formatter.pyi
+++ b/stdlib/@python2/formatter.pyi
@@ -1,37 +1,37 @@
-from typing import IO, Any, Iterable, List, Optional, Tuple
+from typing import IO, Any, Iterable, List, Tuple
 
 AS_IS: None
 _FontType = Tuple[str, bool, bool, bool]
 _StylesType = Tuple[Any, ...]
 
 class NullFormatter:
-    writer: Optional[NullWriter]
-    def __init__(self, writer: Optional[NullWriter] = ...) -> None: ...
+    writer: NullWriter | None
+    def __init__(self, writer: NullWriter | None = ...) -> None: ...
     def end_paragraph(self, blankline: int) -> None: ...
     def add_line_break(self) -> None: ...
     def add_hor_rule(self, *args: Any, **kw: Any) -> None: ...
-    def add_label_data(self, format: str, counter: int, blankline: Optional[int] = ...) -> None: ...
+    def add_label_data(self, format: str, counter: int, blankline: int | None = ...) -> None: ...
     def add_flowing_data(self, data: str) -> None: ...
     def add_literal_data(self, data: str) -> None: ...
     def flush_softspace(self) -> None: ...
-    def push_alignment(self, align: Optional[str]) -> None: ...
+    def push_alignment(self, align: str | None) -> None: ...
     def pop_alignment(self) -> None: ...
     def push_font(self, x: _FontType) -> None: ...
     def pop_font(self) -> None: ...
     def push_margin(self, margin: int) -> None: ...
     def pop_margin(self) -> None: ...
-    def set_spacing(self, spacing: Optional[str]) -> None: ...
+    def set_spacing(self, spacing: str | None) -> None: ...
     def push_style(self, *styles: _StylesType) -> None: ...
     def pop_style(self, n: int = ...) -> None: ...
     def assert_line_data(self, flag: int = ...) -> None: ...
 
 class AbstractFormatter:
     writer: NullWriter
-    align: Optional[str]
-    align_stack: List[Optional[str]]
+    align: str | None
+    align_stack: List[str | None]
     font_stack: List[_FontType]
     margin_stack: List[int]
-    spacing: Optional[str]
+    spacing: str | None
     style_stack: Any
     nospace: int
     softspace: int
@@ -43,20 +43,20 @@ class AbstractFormatter:
     def end_paragraph(self, blankline: int) -> None: ...
     def add_line_break(self) -> None: ...
     def add_hor_rule(self, *args: Any, **kw: Any) -> None: ...
-    def add_label_data(self, format: str, counter: int, blankline: Optional[int] = ...) -> None: ...
+    def add_label_data(self, format: str, counter: int, blankline: int | None = ...) -> None: ...
     def format_counter(self, format: Iterable[str], counter: int) -> str: ...
     def format_letter(self, case: str, counter: int) -> str: ...
     def format_roman(self, case: str, counter: int) -> str: ...
     def add_flowing_data(self, data: str) -> None: ...
     def add_literal_data(self, data: str) -> None: ...
     def flush_softspace(self) -> None: ...
-    def push_alignment(self, align: Optional[str]) -> None: ...
+    def push_alignment(self, align: str | None) -> None: ...
     def pop_alignment(self) -> None: ...
     def push_font(self, font: _FontType) -> None: ...
     def pop_font(self) -> None: ...
     def push_margin(self, margin: int) -> None: ...
     def pop_margin(self) -> None: ...
-    def set_spacing(self, spacing: Optional[str]) -> None: ...
+    def set_spacing(self, spacing: str | None) -> None: ...
     def push_style(self, *styles: _StylesType) -> None: ...
     def pop_style(self, n: int = ...) -> None: ...
     def assert_line_data(self, flag: int = ...) -> None: ...
@@ -64,10 +64,10 @@ class AbstractFormatter:
 class NullWriter:
     def __init__(self) -> None: ...
     def flush(self) -> None: ...
-    def new_alignment(self, align: Optional[str]) -> None: ...
+    def new_alignment(self, align: str | None) -> None: ...
     def new_font(self, font: _FontType) -> None: ...
     def new_margin(self, margin: int, level: int) -> None: ...
-    def new_spacing(self, spacing: Optional[str]) -> None: ...
+    def new_spacing(self, spacing: str | None) -> None: ...
     def new_styles(self, styles: Tuple[Any, ...]) -> None: ...
     def send_paragraph(self, blankline: int) -> None: ...
     def send_line_break(self) -> None: ...
@@ -77,10 +77,10 @@ class NullWriter:
     def send_literal_data(self, data: str) -> None: ...
 
 class AbstractWriter(NullWriter):
-    def new_alignment(self, align: Optional[str]) -> None: ...
+    def new_alignment(self, align: str | None) -> None: ...
     def new_font(self, font: _FontType) -> None: ...
     def new_margin(self, margin: int, level: int) -> None: ...
-    def new_spacing(self, spacing: Optional[str]) -> None: ...
+    def new_spacing(self, spacing: str | None) -> None: ...
     def new_styles(self, styles: Tuple[Any, ...]) -> None: ...
     def send_paragraph(self, blankline: int) -> None: ...
     def send_line_break(self) -> None: ...
@@ -92,7 +92,7 @@ class AbstractWriter(NullWriter):
 class DumbWriter(NullWriter):
     file: IO[str]
     maxcol: int
-    def __init__(self, file: Optional[IO[str]] = ..., maxcol: int = ...) -> None: ...
+    def __init__(self, file: IO[str] | None = ..., maxcol: int = ...) -> None: ...
     def reset(self) -> None: ...
     def send_paragraph(self, blankline: int) -> None: ...
     def send_line_break(self) -> None: ...
@@ -100,4 +100,4 @@ class DumbWriter(NullWriter):
     def send_literal_data(self, data: str) -> None: ...
     def send_flowing_data(self, data: str) -> None: ...
 
-def test(file: Optional[str] = ...) -> None: ...
+def test(file: str | None = ...) -> None: ...
diff --git a/stdlib/@python2/fractions.pyi b/stdlib/@python2/fractions.pyi
index bb60014b398e..872e20ede688 100644
--- a/stdlib/@python2/fractions.pyi
+++ b/stdlib/@python2/fractions.pyi
@@ -1,6 +1,6 @@
 from decimal import Decimal
 from numbers import Integral, Rational, Real
-from typing import Optional, Tuple, Type, TypeVar, Union, overload
+from typing import Tuple, Type, TypeVar, Union, overload
 from typing_extensions import Literal
 
 _ComparableNum = Union[int, float, Decimal, Real]
@@ -18,14 +18,10 @@ def gcd(a: Integral, b: Integral) -> Integral: ...
 class Fraction(Rational):
     @overload
     def __new__(
-        cls: Type[_T],
-        numerator: Union[int, Rational] = ...,
-        denominator: Optional[Union[int, Rational]] = ...,
-        *,
-        _normalize: bool = ...,
+        cls: Type[_T], numerator: int | Rational = ..., denominator: int | Rational | None = ..., *, _normalize: bool = ...
     ) -> _T: ...
     @overload
-    def __new__(cls: Type[_T], __value: Union[float, Decimal, str], *, _normalize: bool = ...) -> _T: ...
+    def __new__(cls: Type[_T], __value: float | Decimal | str, *, _normalize: bool = ...) -> _T: ...
     @classmethod
     def from_float(cls, f: float) -> Fraction: ...
     @classmethod
@@ -36,97 +32,97 @@ class Fraction(Rational):
     @property
     def denominator(self) -> int: ...
     @overload
-    def __add__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __add__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __add__(self, other: float) -> float: ...
     @overload
     def __add__(self, other: complex) -> complex: ...
     @overload
-    def __radd__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __radd__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __radd__(self, other: float) -> float: ...
     @overload
     def __radd__(self, other: complex) -> complex: ...
     @overload
-    def __sub__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __sub__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __sub__(self, other: float) -> float: ...
     @overload
     def __sub__(self, other: complex) -> complex: ...
     @overload
-    def __rsub__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __rsub__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __rsub__(self, other: float) -> float: ...
     @overload
     def __rsub__(self, other: complex) -> complex: ...
     @overload
-    def __mul__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __mul__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __mul__(self, other: float) -> float: ...
     @overload
     def __mul__(self, other: complex) -> complex: ...
     @overload
-    def __rmul__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __rmul__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __rmul__(self, other: float) -> float: ...
     @overload
     def __rmul__(self, other: complex) -> complex: ...
     @overload
-    def __truediv__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __truediv__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __truediv__(self, other: float) -> float: ...
     @overload
     def __truediv__(self, other: complex) -> complex: ...
     @overload
-    def __rtruediv__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __rtruediv__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __rtruediv__(self, other: float) -> float: ...
     @overload
     def __rtruediv__(self, other: complex) -> complex: ...
     @overload
-    def __div__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __div__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __div__(self, other: float) -> float: ...
     @overload
     def __div__(self, other: complex) -> complex: ...
     @overload
-    def __rdiv__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __rdiv__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __rdiv__(self, other: float) -> float: ...
     @overload
     def __rdiv__(self, other: complex) -> complex: ...
     @overload
-    def __floordiv__(self, other: Union[int, Fraction]) -> int: ...
+    def __floordiv__(self, other: int | Fraction) -> int: ...
     @overload
     def __floordiv__(self, other: float) -> float: ...
     @overload
-    def __rfloordiv__(self, other: Union[int, Fraction]) -> int: ...
+    def __rfloordiv__(self, other: int | Fraction) -> int: ...
     @overload
     def __rfloordiv__(self, other: float) -> float: ...
     @overload
-    def __mod__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __mod__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __mod__(self, other: float) -> float: ...
     @overload
-    def __rmod__(self, other: Union[int, Fraction]) -> Fraction: ...
+    def __rmod__(self, other: int | Fraction) -> Fraction: ...
     @overload
     def __rmod__(self, other: float) -> float: ...
     @overload
-    def __divmod__(self, other: Union[int, Fraction]) -> Tuple[int, Fraction]: ...
+    def __divmod__(self, other: int | Fraction) -> Tuple[int, Fraction]: ...
     @overload
     def __divmod__(self, other: float) -> Tuple[float, Fraction]: ...
     @overload
-    def __rdivmod__(self, other: Union[int, Fraction]) -> Tuple[int, Fraction]: ...
+    def __rdivmod__(self, other: int | Fraction) -> Tuple[int, Fraction]: ...
     @overload
     def __rdivmod__(self, other: float) -> Tuple[float, Fraction]: ...
     @overload
     def __pow__(self, other: int) -> Fraction: ...
     @overload
-    def __pow__(self, other: Union[float, Fraction]) -> float: ...
+    def __pow__(self, other: float | Fraction) -> float: ...
     @overload
     def __pow__(self, other: complex) -> complex: ...
     @overload
-    def __rpow__(self, other: Union[int, float, Fraction]) -> float: ...
+    def __rpow__(self, other: int | float | Fraction) -> float: ...
     @overload
     def __rpow__(self, other: complex) -> complex: ...
     def __pos__(self) -> Fraction: ...
diff --git a/stdlib/@python2/ftplib.pyi b/stdlib/@python2/ftplib.pyi
index bdb975fbc21e..0931a9d171cd 100644
--- a/stdlib/@python2/ftplib.pyi
+++ b/stdlib/@python2/ftplib.pyi
@@ -1,7 +1,7 @@
 from _typeshed import SupportsRead, SupportsReadline
 from socket import socket
 from ssl import SSLContext
-from typing import Any, BinaryIO, Callable, List, Optional, Text, Tuple, Type, TypeVar, Union
+from typing import Any, BinaryIO, Callable, List, Text, Tuple, Type, TypeVar, Union
 from typing_extensions import Literal
 
 _T = TypeVar("_T")
@@ -29,14 +29,14 @@ class FTP:
 
     port: int
     maxline: int
-    sock: Optional[socket]
-    welcome: Optional[str]
+    sock: socket | None
+    welcome: str | None
     passiveserver: int
     timeout: int
     af: int
     lastresp: str
 
-    file: Optional[BinaryIO]
+    file: BinaryIO | None
     def __init__(
         self, host: Text = ..., user: Text = ..., passwd: Text = ..., acct: Text = ..., timeout: float = ...
     ) -> None: ...
@@ -44,7 +44,7 @@ class FTP:
     def getwelcome(self) -> str: ...
     def set_debuglevel(self, level: int) -> None: ...
     def debug(self, level: int) -> None: ...
-    def set_pasv(self, val: Union[bool, int]) -> None: ...
+    def set_pasv(self, val: bool | int) -> None: ...
     def sanitize(self, s: Text) -> str: ...
     def putline(self, line: Text) -> None: ...
     def putcmd(self, line: Text) -> None: ...
@@ -61,29 +61,29 @@ class FTP:
     def makepasv(self) -> Tuple[str, int]: ...
     def login(self, user: Text = ..., passwd: Text = ..., acct: Text = ...) -> str: ...
     # In practice, `rest` rest can actually be anything whose str() is an integer sequence, so to make it simple we allow integers.
-    def ntransfercmd(self, cmd: Text, rest: Optional[_IntOrStr] = ...) -> Tuple[socket, int]: ...
-    def transfercmd(self, cmd: Text, rest: Optional[_IntOrStr] = ...) -> socket: ...
+    def ntransfercmd(self, cmd: Text, rest: _IntOrStr | None = ...) -> Tuple[socket, int]: ...
+    def transfercmd(self, cmd: Text, rest: _IntOrStr | None = ...) -> socket: ...
     def retrbinary(
-        self, cmd: Text, callback: Callable[[bytes], Any], blocksize: int = ..., rest: Optional[_IntOrStr] = ...
+        self, cmd: Text, callback: Callable[[bytes], Any], blocksize: int = ..., rest: _IntOrStr | None = ...
     ) -> str: ...
     def storbinary(
         self,
         cmd: Text,
         fp: SupportsRead[bytes],
         blocksize: int = ...,
-        callback: Optional[Callable[[bytes], Any]] = ...,
-        rest: Optional[_IntOrStr] = ...,
+        callback: Callable[[bytes], Any] | None = ...,
+        rest: _IntOrStr | None = ...,
     ) -> str: ...
-    def retrlines(self, cmd: Text, callback: Optional[Callable[[str], Any]] = ...) -> str: ...
-    def storlines(self, cmd: Text, fp: SupportsReadline[bytes], callback: Optional[Callable[[bytes], Any]] = ...) -> str: ...
+    def retrlines(self, cmd: Text, callback: Callable[[str], Any] | None = ...) -> str: ...
+    def storlines(self, cmd: Text, fp: SupportsReadline[bytes], callback: Callable[[bytes], Any] | None = ...) -> str: ...
     def acct(self, password: Text) -> str: ...
     def nlst(self, *args: Text) -> List[str]: ...
     # Technically only the last arg can be a Callable but ...
-    def dir(self, *args: Union[str, Callable[[str], None]]) -> None: ...
+    def dir(self, *args: str | Callable[[str], None]) -> None: ...
     def rename(self, fromname: Text, toname: Text) -> str: ...
     def delete(self, filename: Text) -> str: ...
     def cwd(self, dirname: Text) -> str: ...
-    def size(self, filename: Text) -> Optional[int]: ...
+    def size(self, filename: Text) -> int | None: ...
     def mkd(self, dirname: Text) -> str: ...
     def rmd(self, dirname: Text) -> str: ...
     def pwd(self) -> str: ...
@@ -97,15 +97,15 @@ class FTP_TLS(FTP):
         user: Text = ...,
         passwd: Text = ...,
         acct: Text = ...,
-        keyfile: Optional[str] = ...,
-        certfile: Optional[str] = ...,
-        context: Optional[SSLContext] = ...,
+        keyfile: str | None = ...,
+        certfile: str | None = ...,
+        context: SSLContext | None = ...,
         timeout: float = ...,
-        source_address: Optional[Tuple[str, int]] = ...,
+        source_address: Tuple[str, int] | None = ...,
     ) -> None: ...
     ssl_version: int
-    keyfile: Optional[str]
-    certfile: Optional[str]
+    keyfile: str | None
+    certfile: str | None
     context: SSLContext
     def login(self, user: Text = ..., passwd: Text = ..., acct: Text = ..., secure: bool = ...) -> str: ...
     def auth(self) -> str: ...
@@ -113,13 +113,13 @@ class FTP_TLS(FTP):
     def prot_c(self) -> str: ...
 
 class Netrc:
-    def __init__(self, filename: Optional[Text] = ...) -> None: ...
+    def __init__(self, filename: Text | None = ...) -> None: ...
     def get_hosts(self) -> List[str]: ...
-    def get_account(self, host: Text) -> Tuple[Optional[str], Optional[str], Optional[str]]: ...
+    def get_account(self, host: Text) -> Tuple[str | None, str | None, str | None]: ...
     def get_macros(self) -> List[str]: ...
     def get_macro(self, macro: Text) -> Tuple[str, ...]: ...
 
-def parse150(resp: str) -> Optional[int]: ...  # undocumented
+def parse150(resp: str) -> int | None: ...  # undocumented
 def parse227(resp: str) -> Tuple[str, int]: ...  # undocumented
 def parse229(resp: str, peer: Any) -> Tuple[str, int]: ...  # undocumented
 def parse257(resp: str) -> str: ...  # undocumented
diff --git a/stdlib/@python2/genericpath.pyi b/stdlib/@python2/genericpath.pyi
index f1d3538cd1a4..ba29db4692bb 100644
--- a/stdlib/@python2/genericpath.pyi
+++ b/stdlib/@python2/genericpath.pyi
@@ -6,7 +6,7 @@ from typing_extensions import Literal
 # Iterable[T], so that Union[List[T], Literal[""]] could be used as a return
 # type. But because this only works when T is str, we need Sequence[T] instead.
 @overload
-def commonprefix(m: Sequence[str]) -> Union[str, Literal[""]]: ...  # type: ignore
+def commonprefix(m: Sequence[str]) -> str | Literal[""]: ...  # type: ignore
 @overload
 def commonprefix(m: Sequence[Text]) -> Text: ...  # type: ignore
 @overload
diff --git a/stdlib/@python2/gettext.pyi b/stdlib/@python2/gettext.pyi
index 0930fe63813e..a91234f6b2d3 100644
--- a/stdlib/@python2/gettext.pyi
+++ b/stdlib/@python2/gettext.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, Container, Dict, List, Optional, Sequence, Type, Union
+from typing import IO, Any, Container, Dict, List, Sequence, Type
 
 def bindtextdomain(domain: str, localedir: str = ...) -> str: ...
 def bind_textdomain_codeset(domain: str, codeset: str = ...) -> str: ...
@@ -18,14 +18,14 @@ class NullTranslations(object):
     def add_fallback(self, fallback: NullTranslations) -> None: ...
     def gettext(self, message: str) -> str: ...
     def lgettext(self, message: str) -> str: ...
-    def ugettext(self, message: Union[str, unicode]) -> unicode: ...
+    def ugettext(self, message: str | unicode) -> unicode: ...
     def ngettext(self, singular: str, plural: str, n: int) -> str: ...
     def lngettext(self, singular: str, plural: str, n: int) -> str: ...
-    def ungettext(self, singular: Union[str, unicode], plural: Union[str, unicode], n: int) -> unicode: ...
+    def ungettext(self, singular: str | unicode, plural: str | unicode, n: int) -> unicode: ...
     def info(self) -> Dict[str, str]: ...
-    def charset(self) -> Optional[str]: ...
-    def output_charset(self) -> Optional[str]: ...
-    def set_output_charset(self, charset: Optional[str]) -> None: ...
+    def charset(self) -> str | None: ...
+    def output_charset(self) -> str | None: ...
+    def set_output_charset(self, charset: str | None) -> None: ...
     def install(self, unicode: bool = ..., names: Container[str] = ...) -> None: ...
 
 class GNUTranslations(NullTranslations):
@@ -33,16 +33,16 @@ class GNUTranslations(NullTranslations):
     BE_MAGIC: int
 
 def find(
-    domain: str, localedir: Optional[str] = ..., languages: Optional[Sequence[str]] = ..., all: Any = ...
-) -> Optional[Union[str, List[str]]]: ...
+    domain: str, localedir: str | None = ..., languages: Sequence[str] | None = ..., all: Any = ...
+) -> str | List[str] | None: ...
 def translation(
     domain: str,
-    localedir: Optional[str] = ...,
-    languages: Optional[Sequence[str]] = ...,
-    class_: Optional[Type[NullTranslations]] = ...,
+    localedir: str | None = ...,
+    languages: Sequence[str] | None = ...,
+    class_: Type[NullTranslations] | None = ...,
     fallback: bool = ...,
-    codeset: Optional[str] = ...,
+    codeset: str | None = ...,
 ) -> NullTranslations: ...
 def install(
-    domain: str, localedir: Optional[str] = ..., unicode: bool = ..., codeset: Optional[str] = ..., names: Container[str] = ...
+    domain: str, localedir: str | None = ..., unicode: bool = ..., codeset: str | None = ..., names: Container[str] = ...
 ) -> None: ...
diff --git a/stdlib/@python2/glob.pyi b/stdlib/@python2/glob.pyi
index 2804d74a6a3f..f5a389a0ddfa 100644
--- a/stdlib/@python2/glob.pyi
+++ b/stdlib/@python2/glob.pyi
@@ -1,7 +1,7 @@
-from typing import AnyStr, Iterator, List, Union
+from typing import AnyStr, Iterator, List
 
 def glob(pathname: AnyStr) -> List[AnyStr]: ...
 def iglob(pathname: AnyStr) -> Iterator[AnyStr]: ...
-def glob1(dirname: Union[str, unicode], pattern: AnyStr) -> List[AnyStr]: ...
-def glob0(dirname: Union[str, unicode], basename: AnyStr) -> List[AnyStr]: ...
-def has_magic(s: Union[str, unicode]) -> bool: ...  # undocumented
+def glob1(dirname: str | unicode, pattern: AnyStr) -> List[AnyStr]: ...
+def glob0(dirname: str | unicode, basename: AnyStr) -> List[AnyStr]: ...
+def has_magic(s: str | unicode) -> bool: ...  # undocumented
diff --git a/stdlib/@python2/grp.pyi b/stdlib/@python2/grp.pyi
index 8447f21736bb..63898b26bf17 100644
--- a/stdlib/@python2/grp.pyi
+++ b/stdlib/@python2/grp.pyi
@@ -1,8 +1,8 @@
-from typing import List, NamedTuple, Optional
+from typing import List, NamedTuple
 
 class struct_group(NamedTuple):
     gr_name: str
-    gr_passwd: Optional[str]
+    gr_passwd: str | None
     gr_gid: int
     gr_mem: List[str]
 
diff --git a/stdlib/@python2/heapq.pyi b/stdlib/@python2/heapq.pyi
index 8bdb3d23b9ba..78ce6fd03928 100644
--- a/stdlib/@python2/heapq.pyi
+++ b/stdlib/@python2/heapq.pyi
@@ -1,5 +1,5 @@
 from _typeshed import SupportsLessThan
-from typing import Callable, Iterable, List, Optional, TypeVar
+from typing import Callable, Iterable, List, TypeVar
 
 _T = TypeVar("_T")
 
@@ -10,6 +10,6 @@ def heappushpop(heap: List[_T], item: _T) -> _T: ...
 def heapify(x: List[_T]) -> None: ...
 def heapreplace(heap: List[_T], item: _T) -> _T: ...
 def merge(*iterables: Iterable[_T]) -> Iterable[_T]: ...
-def nlargest(n: int, iterable: Iterable[_T], key: Optional[Callable[[_T], SupportsLessThan]] = ...) -> List[_T]: ...
-def nsmallest(n: int, iterable: Iterable[_T], key: Optional[Callable[[_T], SupportsLessThan]] = ...) -> List[_T]: ...
+def nlargest(n: int, iterable: Iterable[_T], key: Callable[[_T], SupportsLessThan] | None = ...) -> List[_T]: ...
+def nsmallest(n: int, iterable: Iterable[_T], key: Callable[[_T], SupportsLessThan] | None = ...) -> List[_T]: ...
 def _heapify_max(__x: List[_T]) -> None: ...  # undocumented
diff --git a/stdlib/@python2/hmac.pyi b/stdlib/@python2/hmac.pyi
index 7550163b6707..cc39d8c65c8f 100644
--- a/stdlib/@python2/hmac.pyi
+++ b/stdlib/@python2/hmac.pyi
@@ -1,6 +1,6 @@
 from _typeshed import ReadableBuffer
 from types import ModuleType
-from typing import Any, AnyStr, Callable, Optional, Union, overload
+from typing import Any, AnyStr, Callable, Union, overload
 
 # TODO more precise type for object of hashlib
 _Hash = Any
@@ -8,10 +8,10 @@ _DigestMod = Union[str, Callable[[], _Hash], ModuleType]
 
 digest_size: None
 
-def new(key: bytes, msg: Optional[ReadableBuffer] = ..., digestmod: Optional[_DigestMod] = ...) -> HMAC: ...
+def new(key: bytes, msg: ReadableBuffer | None = ..., digestmod: _DigestMod | None = ...) -> HMAC: ...
 
 class HMAC:
-    def __init__(self, key: bytes, msg: Optional[ReadableBuffer] = ..., digestmod: _DigestMod = ...) -> None: ...
+    def __init__(self, key: bytes, msg: ReadableBuffer | None = ..., digestmod: _DigestMod = ...) -> None: ...
     def update(self, msg: ReadableBuffer) -> None: ...
     def digest(self) -> bytes: ...
     def hexdigest(self) -> str: ...
diff --git a/stdlib/@python2/httplib.pyi b/stdlib/@python2/httplib.pyi
index 6901dfc0f695..f2163818fae4 100644
--- a/stdlib/@python2/httplib.pyi
+++ b/stdlib/@python2/httplib.pyi
@@ -1,5 +1,5 @@
 import mimetools
-from typing import Any, Dict, Optional, Protocol
+from typing import Any, Dict, Protocol
 
 class HTTPMessage(mimetools.Message):
     def addcontinue(self, key: str, more: str) -> None: ...
@@ -24,14 +24,14 @@ class HTTPResponse:
     length: Any
     will_close: Any
     def __init__(
-        self, sock, debuglevel: int = ..., strict: int = ..., method: Optional[Any] = ..., buffering: bool = ...
+        self, sock, debuglevel: int = ..., strict: int = ..., method: Any | None = ..., buffering: bool = ...
     ) -> None: ...
     def begin(self): ...
     def close(self): ...
     def isclosed(self): ...
-    def read(self, amt: Optional[Any] = ...): ...
+    def read(self, amt: Any | None = ...): ...
     def fileno(self): ...
-    def getheader(self, name, default: Optional[Any] = ...): ...
+    def getheader(self, name, default: Any | None = ...): ...
     def getheaders(self): ...
 
 # This is an API stub only for HTTPConnection and HTTPSConnection, as used in
@@ -55,23 +55,23 @@ class HTTPConnection:
     host: str = ...
     port: int = ...
     def __init__(
-        self, host, port: Optional[Any] = ..., strict: Optional[Any] = ..., timeout=..., source_address: Optional[Any] = ...
+        self, host, port: Any | None = ..., strict: Any | None = ..., timeout=..., source_address: Any | None = ...
     ) -> None: ...
-    def set_tunnel(self, host, port: Optional[Any] = ..., headers: Optional[Any] = ...): ...
+    def set_tunnel(self, host, port: Any | None = ..., headers: Any | None = ...): ...
     def set_debuglevel(self, level): ...
     def connect(self): ...
     def close(self): ...
     def send(self, data): ...
     def putrequest(self, method, url, skip_host: int = ..., skip_accept_encoding: int = ...): ...
     def putheader(self, header, *values): ...
-    def endheaders(self, message_body: Optional[Any] = ...): ...
-    def request(self, method, url, body: Optional[Any] = ..., headers=...): ...
+    def endheaders(self, message_body: Any | None = ...): ...
+    def request(self, method, url, body: Any | None = ..., headers=...): ...
     def getresponse(self, buffering: bool = ...): ...
 
 class HTTP:
     debuglevel: Any
-    def __init__(self, host: str = ..., port: Optional[Any] = ..., strict: Optional[Any] = ...) -> None: ...
-    def connect(self, host: Optional[Any] = ..., port: Optional[Any] = ...): ...
+    def __init__(self, host: str = ..., port: Any | None = ..., strict: Any | None = ...) -> None: ...
+    def connect(self, host: Any | None = ..., port: Any | None = ...): ...
     def getfile(self): ...
     file: Any
     headers: Any
@@ -85,13 +85,13 @@ class HTTPSConnection(HTTPConnection):
     def __init__(
         self,
         host,
-        port: Optional[Any] = ...,
-        key_file: Optional[Any] = ...,
-        cert_file: Optional[Any] = ...,
-        strict: Optional[Any] = ...,
+        port: Any | None = ...,
+        key_file: Any | None = ...,
+        cert_file: Any | None = ...,
+        strict: Any | None = ...,
         timeout=...,
-        source_address: Optional[Any] = ...,
-        context: Optional[Any] = ...,
+        source_address: Any | None = ...,
+        context: Any | None = ...,
     ) -> None: ...
     sock: Any
     def connect(self): ...
@@ -102,11 +102,11 @@ class HTTPS(HTTP):
     def __init__(
         self,
         host: str = ...,
-        port: Optional[Any] = ...,
-        key_file: Optional[Any] = ...,
-        cert_file: Optional[Any] = ...,
-        strict: Optional[Any] = ...,
-        context: Optional[Any] = ...,
+        port: Any | None = ...,
+        key_file: Any | None = ...,
+        cert_file: Any | None = ...,
+        strict: Any | None = ...,
+        context: Any | None = ...,
     ) -> None: ...
 
 class HTTPException(Exception): ...
@@ -125,7 +125,7 @@ class IncompleteRead(HTTPException):
     args: Any
     partial: Any
     expected: Any
-    def __init__(self, partial, expected: Optional[Any] = ...) -> None: ...
+    def __init__(self, partial, expected: Any | None = ...) -> None: ...
 
 class ImproperConnectionState(HTTPException): ...
 class CannotSendRequest(ImproperConnectionState): ...
@@ -145,9 +145,9 @@ error: Any
 class LineAndFileWrapper:
     def __init__(self, line, file) -> None: ...
     def __getattr__(self, attr): ...
-    def read(self, amt: Optional[Any] = ...): ...
+    def read(self, amt: Any | None = ...): ...
     def readline(self): ...
-    def readlines(self, size: Optional[Any] = ...): ...
+    def readlines(self, size: Any | None = ...): ...
 
 # Constants
 
diff --git a/stdlib/@python2/imaplib.pyi b/stdlib/@python2/imaplib.pyi
index 73063629295a..c4346851bdac 100644
--- a/stdlib/@python2/imaplib.pyi
+++ b/stdlib/@python2/imaplib.pyi
@@ -2,7 +2,7 @@ import subprocess
 import time
 from socket import socket as _socket
 from ssl import SSLSocket
-from typing import IO, Any, Callable, Dict, List, Optional, Pattern, Text, Tuple, Type, Union
+from typing import IO, Any, Callable, Dict, List, Pattern, Text, Tuple, Type, Union
 from typing_extensions import Literal
 
 # TODO: Commands should use their actual return types, not this type alias.
@@ -18,9 +18,9 @@ class IMAP4:
     mustquote: Pattern[Text] = ...
     debug: int = ...
     state: str = ...
-    literal: Optional[Text] = ...
-    tagged_commands: Dict[bytes, Optional[List[bytes]]]
-    untagged_responses: Dict[str, List[Union[bytes, Tuple[bytes, bytes]]]]
+    literal: Text | None = ...
+    tagged_commands: Dict[bytes, List[bytes] | None]
+    untagged_responses: Dict[str, List[bytes | Tuple[bytes, bytes]]]
     continuation_response: str = ...
     is_readonly: bool = ...
     tagnum: int = ...
@@ -35,7 +35,7 @@ class IMAP4:
     host: str = ...
     port: int = ...
     sock: _socket = ...
-    file: Union[IO[Text], IO[bytes]] = ...
+    file: IO[Text] | IO[bytes] = ...
     def read(self, size: int) -> bytes: ...
     def readline(self) -> bytes: ...
     def send(self, data: bytes) -> None: ...
@@ -44,7 +44,7 @@ class IMAP4:
     def recent(self) -> _CommandResults: ...
     def response(self, code: str) -> _CommandResults: ...
     def append(self, mailbox: str, flags: str, date_time: str, message: str) -> str: ...
-    def authenticate(self, mechanism: str, authobject: Callable[[bytes], Optional[bytes]]) -> Tuple[str, str]: ...
+    def authenticate(self, mechanism: str, authobject: Callable[[bytes], bytes | None]) -> Tuple[str, str]: ...
     def capability(self) -> _CommandResults: ...
     def check(self) -> _CommandResults: ...
     def close(self) -> _CommandResults: ...
@@ -69,8 +69,8 @@ class IMAP4:
     def partial(self, message_num: str, message_part: str, start: str, length: str) -> _CommandResults: ...
     def proxyauth(self, user: str) -> _CommandResults: ...
     def rename(self, oldmailbox: str, newmailbox: str) -> _CommandResults: ...
-    def search(self, charset: Optional[str], *criteria: str) -> _CommandResults: ...
-    def select(self, mailbox: str = ..., readonly: bool = ...) -> Tuple[str, List[Optional[bytes]]]: ...
+    def search(self, charset: str | None, *criteria: str) -> _CommandResults: ...
+    def select(self, mailbox: str = ..., readonly: bool = ...) -> Tuple[str, List[bytes | None]]: ...
     def setacl(self, mailbox: str, who: str, what: str) -> _CommandResults: ...
     def setannotation(self, *args: str) -> _CommandResults: ...
     def setquota(self, root: str, limits: str) -> _CommandResults: ...
@@ -87,13 +87,13 @@ class IMAP4:
 class IMAP4_SSL(IMAP4):
     keyfile: str = ...
     certfile: str = ...
-    def __init__(self, host: str = ..., port: int = ..., keyfile: Optional[str] = ..., certfile: Optional[str] = ...) -> None: ...
+    def __init__(self, host: str = ..., port: int = ..., keyfile: str | None = ..., certfile: str | None = ...) -> None: ...
     host: str = ...
     port: int = ...
     sock: _socket = ...
     sslobj: SSLSocket = ...
     file: IO[Any] = ...
-    def open(self, host: str = ..., port: Optional[int] = ...) -> None: ...
+    def open(self, host: str = ..., port: int | None = ...) -> None: ...
     def read(self, size: int) -> bytes: ...
     def readline(self) -> bytes: ...
     def send(self, data: bytes) -> None: ...
@@ -111,7 +111,7 @@ class IMAP4_stream(IMAP4):
     process: subprocess.Popen[bytes] = ...
     writefile: IO[Any] = ...
     readfile: IO[Any] = ...
-    def open(self, host: Optional[str] = ..., port: Optional[int] = ...) -> None: ...
+    def open(self, host: str | None = ..., port: int | None = ...) -> None: ...
     def read(self, size: int) -> bytes: ...
     def readline(self) -> bytes: ...
     def send(self, data: bytes) -> None: ...
@@ -127,4 +127,4 @@ class _Authenticator:
 def Internaldate2tuple(resp: str) -> time.struct_time: ...
 def Int2AP(num: int) -> str: ...
 def ParseFlags(resp: str) -> Tuple[str]: ...
-def Time2Internaldate(date_time: Union[float, time.struct_time, str]) -> str: ...
+def Time2Internaldate(date_time: float | time.struct_time | str) -> str: ...
diff --git a/stdlib/@python2/imghdr.pyi b/stdlib/@python2/imghdr.pyi
index 4a6c3f39eb27..d60cafa4c78f 100644
--- a/stdlib/@python2/imghdr.pyi
+++ b/stdlib/@python2/imghdr.pyi
@@ -1,4 +1,4 @@
-from typing import Any, BinaryIO, Callable, List, Optional, Protocol, Text, Union, overload
+from typing import Any, BinaryIO, Callable, List, Protocol, Text, Union, overload
 
 class _ReadableBinary(Protocol):
     def tell(self) -> int: ...
@@ -8,8 +8,8 @@ class _ReadableBinary(Protocol):
 _File = Union[Text, _ReadableBinary]
 
 @overload
-def what(file: _File, h: None = ...) -> Optional[str]: ...
+def what(file: _File, h: None = ...) -> str | None: ...
 @overload
-def what(file: Any, h: bytes) -> Optional[str]: ...
+def what(file: Any, h: bytes) -> str | None: ...
 
-tests: List[Callable[[bytes, Optional[BinaryIO]], Optional[str]]]
+tests: List[Callable[[bytes, BinaryIO | None], str | None]]
diff --git a/stdlib/@python2/imp.pyi b/stdlib/@python2/imp.pyi
index 3cd37648b968..128bd900e996 100644
--- a/stdlib/@python2/imp.pyi
+++ b/stdlib/@python2/imp.pyi
@@ -1,5 +1,5 @@
 import types
-from typing import IO, Any, Iterable, List, Optional, Tuple
+from typing import IO, Any, Iterable, List, Tuple
 
 C_BUILTIN: int
 C_EXTENSION: int
@@ -13,7 +13,7 @@ PY_SOURCE: int
 SEARCH_ERROR: int
 
 def acquire_lock() -> None: ...
-def find_module(name: str, path: Iterable[str] = ...) -> Optional[Tuple[IO[Any], str, Tuple[str, str, int]]]: ...
+def find_module(name: str, path: Iterable[str] = ...) -> Tuple[IO[Any], str, Tuple[str, str, int]] | None: ...
 def get_magic() -> str: ...
 def get_suffixes() -> List[Tuple[str, str, int]]: ...
 def init_builtin(name: str) -> types.ModuleType: ...
diff --git a/stdlib/@python2/importlib.pyi b/stdlib/@python2/importlib.pyi
index 8bb179a4bd9a..530cb1a3c79c 100644
--- a/stdlib/@python2/importlib.pyi
+++ b/stdlib/@python2/importlib.pyi
@@ -1,4 +1,4 @@
 import types
-from typing import Optional, Text
+from typing import Text
 
-def import_module(name: Text, package: Optional[Text] = ...) -> types.ModuleType: ...
+def import_module(name: Text, package: Text | None = ...) -> types.ModuleType: ...
diff --git a/stdlib/@python2/inspect.pyi b/stdlib/@python2/inspect.pyi
index 8e95a92cac10..c6118ea8aebb 100644
--- a/stdlib/@python2/inspect.pyi
+++ b/stdlib/@python2/inspect.pyi
@@ -29,9 +29,9 @@ class ModuleInfo(NamedTuple):
     mode: str
     module_type: int
 
-def getmembers(object: object, predicate: Optional[Callable[[Any], bool]] = ...) -> List[Tuple[str, Any]]: ...
-def getmoduleinfo(path: Union[str, unicode]) -> Optional[ModuleInfo]: ...
-def getmodulename(path: AnyStr) -> Optional[AnyStr]: ...
+def getmembers(object: object, predicate: Callable[[Any], bool] | None = ...) -> List[Tuple[str, Any]]: ...
+def getmoduleinfo(path: str | unicode) -> ModuleInfo | None: ...
+def getmodulename(path: AnyStr) -> AnyStr | None: ...
 def ismodule(object: object) -> bool: ...
 def isclass(object: object) -> bool: ...
 def ismethod(object: object) -> bool: ...
@@ -55,35 +55,35 @@ _SourceObjectType = Union[ModuleType, Type[Any], MethodType, FunctionType, Trace
 def findsource(object: _SourceObjectType) -> Tuple[List[str], int]: ...
 def getabsfile(object: _SourceObjectType) -> str: ...
 def getblock(lines: Sequence[AnyStr]) -> Sequence[AnyStr]: ...
-def getdoc(object: object) -> Optional[str]: ...
-def getcomments(object: object) -> Optional[str]: ...
+def getdoc(object: object) -> str | None: ...
+def getcomments(object: object) -> str | None: ...
 def getfile(object: _SourceObjectType) -> str: ...
-def getmodule(object: object) -> Optional[ModuleType]: ...
-def getsourcefile(object: _SourceObjectType) -> Optional[str]: ...
+def getmodule(object: object) -> ModuleType | None: ...
+def getsourcefile(object: _SourceObjectType) -> str | None: ...
 def getsourcelines(object: _SourceObjectType) -> Tuple[List[str], int]: ...
 def getsource(object: _SourceObjectType) -> str: ...
 def cleandoc(doc: AnyStr) -> AnyStr: ...
-def indentsize(line: Union[str, unicode]) -> int: ...
+def indentsize(line: str | unicode) -> int: ...
 
 # Classes and functions
-def getclasstree(classes: List[type], unique: bool = ...) -> List[Union[Tuple[type, Tuple[type, ...]], List[Any]]]: ...
+def getclasstree(classes: List[type], unique: bool = ...) -> List[Tuple[type, Tuple[type, ...]] | List[Any]]: ...
 
 class ArgSpec(NamedTuple):
     args: List[str]
-    varargs: Optional[str]
-    keywords: Optional[str]
+    varargs: str | None
+    keywords: str | None
     defaults: Tuple[Any, ...]
 
 class ArgInfo(NamedTuple):
     args: List[str]
-    varargs: Optional[str]
-    keywords: Optional[str]
+    varargs: str | None
+    keywords: str | None
     locals: Dict[str, Any]
 
 class Arguments(NamedTuple):
-    args: List[Union[str, List[Any]]]
-    varargs: Optional[str]
-    keywords: Optional[str]
+    args: List[str | List[Any]]
+    varargs: str | None
+    keywords: str | None
 
 def getargs(co: CodeType) -> Arguments: ...
 def getargspec(func: object) -> ArgSpec: ...
@@ -103,13 +103,13 @@ class Traceback(NamedTuple):
     filename: str
     lineno: int
     function: str
-    code_context: Optional[List[str]]
-    index: Optional[int]  # type: ignore
+    code_context: List[str] | None
+    index: int | None  # type: ignore
 
 _FrameInfo = Tuple[FrameType, str, int, str, Optional[List[str]], Optional[int]]
 
 def getouterframes(frame: FrameType, context: int = ...) -> List[_FrameInfo]: ...
-def getframeinfo(frame: Union[FrameType, TracebackType], context: int = ...) -> Traceback: ...
+def getframeinfo(frame: FrameType | TracebackType, context: int = ...) -> Traceback: ...
 def getinnerframes(traceback: TracebackType, context: int = ...) -> List[_FrameInfo]: ...
 def getlineno(frame: FrameType) -> int: ...
 def currentframe(depth: int = ...) -> FrameType: ...
diff --git a/stdlib/@python2/io.pyi b/stdlib/@python2/io.pyi
index 1e29cc67369f..f36138edd598 100644
--- a/stdlib/@python2/io.pyi
+++ b/stdlib/@python2/io.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, Union
+from typing import IO, Any
 
 import _io
 from _io import (
@@ -18,7 +18,7 @@ from _io import (
 )
 
 def _OpenWrapper(
-    file: Union[str, unicode, int],
+    file: str | unicode | int,
     mode: unicode = ...,
     buffering: int = ...,
     encoding: unicode = ...,
diff --git a/stdlib/@python2/itertools.pyi b/stdlib/@python2/itertools.pyi
index 63c38980ce79..12996d44628b 100644
--- a/stdlib/@python2/itertools.pyi
+++ b/stdlib/@python2/itertools.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, Generic, Iterable, Iterator, Optional, Sequence, Tuple, TypeVar, overload
+from typing import Any, Callable, Generic, Iterable, Iterator, Sequence, Tuple, TypeVar, overload
 
 _T = TypeVar("_T")
 _S = TypeVar("_S")
@@ -21,16 +21,16 @@ class chain(Iterator[_T], Generic[_T]):
 
 def compress(data: Iterable[_T], selectors: Iterable[Any]) -> Iterator[_T]: ...
 def dropwhile(predicate: Callable[[_T], Any], iterable: Iterable[_T]) -> Iterator[_T]: ...
-def ifilter(predicate: Optional[Callable[[_T], Any]], iterable: Iterable[_T]) -> Iterator[_T]: ...
-def ifilterfalse(predicate: Optional[Callable[[_T], Any]], iterable: Iterable[_T]) -> Iterator[_T]: ...
+def ifilter(predicate: Callable[[_T], Any] | None, iterable: Iterable[_T]) -> Iterator[_T]: ...
+def ifilterfalse(predicate: Callable[[_T], Any] | None, iterable: Iterable[_T]) -> Iterator[_T]: ...
 @overload
 def groupby(iterable: Iterable[_T], key: None = ...) -> Iterator[Tuple[_T, Iterator[_T]]]: ...
 @overload
 def groupby(iterable: Iterable[_T], key: Callable[[_T], _S]) -> Iterator[Tuple[_S, Iterator[_T]]]: ...
 @overload
-def islice(iterable: Iterable[_T], stop: Optional[int]) -> Iterator[_T]: ...
+def islice(iterable: Iterable[_T], stop: int | None) -> Iterator[_T]: ...
 @overload
-def islice(iterable: Iterable[_T], start: Optional[int], stop: Optional[int], step: Optional[int] = ...) -> Iterator[_T]: ...
+def islice(iterable: Iterable[_T], start: int | None, stop: int | None, step: int | None = ...) -> Iterator[_T]: ...
 
 _T1 = TypeVar("_T1")
 _T2 = TypeVar("_T2")
diff --git a/stdlib/@python2/json.pyi b/stdlib/@python2/json.pyi
index 2d38e6b47bb8..bfbddb2a6835 100644
--- a/stdlib/@python2/json.pyi
+++ b/stdlib/@python2/json.pyi
@@ -1,5 +1,5 @@
 from _typeshed import SupportsRead
-from typing import IO, Any, Callable, Dict, List, Optional, Text, Tuple, Type, Union
+from typing import IO, Any, Callable, Dict, List, Text, Tuple, Type
 
 def dumps(
     obj: Any,
@@ -7,56 +7,56 @@ def dumps(
     ensure_ascii: bool = ...,
     check_circular: bool = ...,
     allow_nan: bool = ...,
-    cls: Optional[Type[JSONEncoder]] = ...,
-    indent: Optional[int] = ...,
-    separators: Optional[Tuple[str, str]] = ...,
+    cls: Type[JSONEncoder] | None = ...,
+    indent: int | None = ...,
+    separators: Tuple[str, str] | None = ...,
     encoding: str = ...,
-    default: Optional[Callable[[Any], Any]] = ...,
+    default: Callable[[Any], Any] | None = ...,
     sort_keys: bool = ...,
     **kwds: Any,
 ) -> str: ...
 def dump(
     obj: Any,
-    fp: Union[IO[str], IO[Text]],
+    fp: IO[str] | IO[Text],
     skipkeys: bool = ...,
     ensure_ascii: bool = ...,
     check_circular: bool = ...,
     allow_nan: bool = ...,
-    cls: Optional[Type[JSONEncoder]] = ...,
-    indent: Optional[int] = ...,
-    separators: Optional[Tuple[str, str]] = ...,
+    cls: Type[JSONEncoder] | None = ...,
+    indent: int | None = ...,
+    separators: Tuple[str, str] | None = ...,
     encoding: str = ...,
-    default: Optional[Callable[[Any], Any]] = ...,
+    default: Callable[[Any], Any] | None = ...,
     sort_keys: bool = ...,
     **kwds: Any,
 ) -> None: ...
 def loads(
-    s: Union[Text, bytes],
+    s: Text | bytes,
     encoding: Any = ...,
-    cls: Optional[Type[JSONDecoder]] = ...,
-    object_hook: Optional[Callable[[Dict[Any, Any]], Any]] = ...,
-    parse_float: Optional[Callable[[str], Any]] = ...,
-    parse_int: Optional[Callable[[str], Any]] = ...,
-    parse_constant: Optional[Callable[[str], Any]] = ...,
-    object_pairs_hook: Optional[Callable[[List[Tuple[Any, Any]]], Any]] = ...,
+    cls: Type[JSONDecoder] | None = ...,
+    object_hook: Callable[[Dict[Any, Any]], Any] | None = ...,
+    parse_float: Callable[[str], Any] | None = ...,
+    parse_int: Callable[[str], Any] | None = ...,
+    parse_constant: Callable[[str], Any] | None = ...,
+    object_pairs_hook: Callable[[List[Tuple[Any, Any]]], Any] | None = ...,
     **kwds: Any,
 ) -> Any: ...
 def load(
-    fp: SupportsRead[Union[Text, bytes]],
-    encoding: Optional[str] = ...,
-    cls: Optional[Type[JSONDecoder]] = ...,
-    object_hook: Optional[Callable[[Dict[Any, Any]], Any]] = ...,
-    parse_float: Optional[Callable[[str], Any]] = ...,
-    parse_int: Optional[Callable[[str], Any]] = ...,
-    parse_constant: Optional[Callable[[str], Any]] = ...,
-    object_pairs_hook: Optional[Callable[[List[Tuple[Any, Any]]], Any]] = ...,
+    fp: SupportsRead[Text | bytes],
+    encoding: str | None = ...,
+    cls: Type[JSONDecoder] | None = ...,
+    object_hook: Callable[[Dict[Any, Any]], Any] | None = ...,
+    parse_float: Callable[[str], Any] | None = ...,
+    parse_int: Callable[[str], Any] | None = ...,
+    parse_constant: Callable[[str], Any] | None = ...,
+    object_pairs_hook: Callable[[List[Tuple[Any, Any]]], Any] | None = ...,
     **kwds: Any,
 ) -> Any: ...
 
 class JSONDecoder(object):
     def __init__(
         self,
-        encoding: Union[Text, bytes] = ...,
+        encoding: Text | bytes = ...,
         object_hook: Callable[..., Any] = ...,
         parse_float: Callable[[str], float] = ...,
         parse_int: Callable[[str], int] = ...,
@@ -64,8 +64,8 @@ class JSONDecoder(object):
         strict: bool = ...,
         object_pairs_hook: Callable[..., Any] = ...,
     ) -> None: ...
-    def decode(self, s: Union[Text, bytes], _w: Any = ...) -> Any: ...
-    def raw_decode(self, s: Union[Text, bytes], idx: int = ...) -> Tuple[Any, Any]: ...
+    def decode(self, s: Text | bytes, _w: Any = ...) -> Any: ...
+    def raw_decode(self, s: Text | bytes, idx: int = ...) -> Tuple[Any, Any]: ...
 
 class JSONEncoder(object):
     item_separator: str
@@ -75,7 +75,7 @@ class JSONEncoder(object):
     check_circular: bool
     allow_nan: bool
     sort_keys: bool
-    indent: Optional[int]
+    indent: int | None
     def __init__(
         self,
         skipkeys: bool = ...,
@@ -83,9 +83,9 @@ class JSONEncoder(object):
         check_circular: bool = ...,
         allow_nan: bool = ...,
         sort_keys: bool = ...,
-        indent: Optional[int] = ...,
-        separators: Tuple[Union[Text, bytes], Union[Text, bytes]] = ...,
-        encoding: Union[Text, bytes] = ...,
+        indent: int | None = ...,
+        separators: Tuple[Text | bytes, Text | bytes] = ...,
+        encoding: Text | bytes = ...,
         default: Callable[..., Any] = ...,
     ) -> None: ...
     def default(self, o: Any) -> Any: ...
diff --git a/stdlib/@python2/lib2to3/pgen2/driver.pyi b/stdlib/@python2/lib2to3/pgen2/driver.pyi
index 841b0e4b1cb3..f36e3dd0a10c 100644
--- a/stdlib/@python2/lib2to3/pgen2/driver.pyi
+++ b/stdlib/@python2/lib2to3/pgen2/driver.pyi
@@ -2,19 +2,19 @@ from _typeshed import StrPath
 from lib2to3.pgen2.grammar import Grammar
 from lib2to3.pytree import _NL, _Convert
 from logging import Logger
-from typing import IO, Any, Iterable, Optional, Text
+from typing import IO, Any, Iterable, Text
 
 class Driver:
     grammar: Grammar
     logger: Logger
     convert: _Convert
-    def __init__(self, grammar: Grammar, convert: Optional[_Convert] = ..., logger: Optional[Logger] = ...) -> None: ...
+    def __init__(self, grammar: Grammar, convert: _Convert | None = ..., logger: Logger | None = ...) -> None: ...
     def parse_tokens(self, tokens: Iterable[Any], debug: bool = ...) -> _NL: ...
     def parse_stream_raw(self, stream: IO[Text], debug: bool = ...) -> _NL: ...
     def parse_stream(self, stream: IO[Text], debug: bool = ...) -> _NL: ...
-    def parse_file(self, filename: StrPath, encoding: Optional[Text] = ..., debug: bool = ...) -> _NL: ...
+    def parse_file(self, filename: StrPath, encoding: Text | None = ..., debug: bool = ...) -> _NL: ...
     def parse_string(self, text: Text, debug: bool = ...) -> _NL: ...
 
 def load_grammar(
-    gt: Text = ..., gp: Optional[Text] = ..., save: bool = ..., force: bool = ..., logger: Optional[Logger] = ...
+    gt: Text = ..., gp: Text | None = ..., save: bool = ..., force: bool = ..., logger: Logger | None = ...
 ) -> Grammar: ...
diff --git a/stdlib/@python2/lib2to3/pgen2/parse.pyi b/stdlib/@python2/lib2to3/pgen2/parse.pyi
index b7018cba9c1d..eed165db551c 100644
--- a/stdlib/@python2/lib2to3/pgen2/parse.pyi
+++ b/stdlib/@python2/lib2to3/pgen2/parse.pyi
@@ -1,26 +1,26 @@
 from lib2to3.pgen2.grammar import _DFAS, Grammar
 from lib2to3.pytree import _NL, _Convert, _RawNode
-from typing import Any, List, Optional, Sequence, Set, Text, Tuple
+from typing import Any, List, Sequence, Set, Text, Tuple
 
 _Context = Sequence[Any]
 
 class ParseError(Exception):
     msg: Text
     type: int
-    value: Optional[Text]
+    value: Text | None
     context: _Context
-    def __init__(self, msg: Text, type: int, value: Optional[Text], context: _Context) -> None: ...
+    def __init__(self, msg: Text, type: int, value: Text | None, context: _Context) -> None: ...
 
 class Parser:
     grammar: Grammar
     convert: _Convert
     stack: List[Tuple[_DFAS, int, _RawNode]]
-    rootnode: Optional[_NL]
+    rootnode: _NL | None
     used_names: Set[Text]
-    def __init__(self, grammar: Grammar, convert: Optional[_Convert] = ...) -> None: ...
-    def setup(self, start: Optional[int] = ...) -> None: ...
-    def addtoken(self, type: int, value: Optional[Text], context: _Context) -> bool: ...
-    def classify(self, type: int, value: Optional[Text], context: _Context) -> int: ...
-    def shift(self, type: int, value: Optional[Text], newstate: int, context: _Context) -> None: ...
+    def __init__(self, grammar: Grammar, convert: _Convert | None = ...) -> None: ...
+    def setup(self, start: int | None = ...) -> None: ...
+    def addtoken(self, type: int, value: Text | None, context: _Context) -> bool: ...
+    def classify(self, type: int, value: Text | None, context: _Context) -> int: ...
+    def shift(self, type: int, value: Text | None, newstate: int, context: _Context) -> None: ...
     def push(self, type: int, newdfa: _DFAS, newstate: int, context: _Context) -> None: ...
     def pop(self) -> None: ...
diff --git a/stdlib/@python2/lib2to3/pgen2/pgen.pyi b/stdlib/@python2/lib2to3/pgen2/pgen.pyi
index 7920262f4f04..67dbbccdd4a6 100644
--- a/stdlib/@python2/lib2to3/pgen2/pgen.pyi
+++ b/stdlib/@python2/lib2to3/pgen2/pgen.pyi
@@ -1,7 +1,7 @@
 from _typeshed import StrPath
 from lib2to3.pgen2 import grammar
 from lib2to3.pgen2.tokenize import _TokenInfo
-from typing import IO, Any, Dict, Iterable, Iterator, List, NoReturn, Optional, Text, Tuple
+from typing import IO, Any, Dict, Iterable, Iterator, List, NoReturn, Text, Tuple
 
 class PgenGrammar(grammar.Grammar): ...
 
@@ -10,7 +10,7 @@ class ParserGenerator:
     stream: IO[Text]
     generator: Iterator[_TokenInfo]
     first: Dict[Text, Dict[Text, int]]
-    def __init__(self, filename: StrPath, stream: Optional[IO[Text]] = ...) -> None: ...
+    def __init__(self, filename: StrPath, stream: IO[Text] | None = ...) -> None: ...
     def make_grammar(self) -> PgenGrammar: ...
     def make_first(self, c: PgenGrammar, name: Text) -> Dict[int, int]: ...
     def make_label(self, c: PgenGrammar, label: Text) -> int: ...
@@ -25,14 +25,14 @@ class ParserGenerator:
     def parse_alt(self) -> Tuple[NFAState, NFAState]: ...
     def parse_item(self) -> Tuple[NFAState, NFAState]: ...
     def parse_atom(self) -> Tuple[NFAState, NFAState]: ...
-    def expect(self, type: int, value: Optional[Any] = ...) -> Text: ...
+    def expect(self, type: int, value: Any | None = ...) -> Text: ...
     def gettoken(self) -> None: ...
     def raise_error(self, msg: str, *args: Any) -> NoReturn: ...
 
 class NFAState:
-    arcs: List[Tuple[Optional[Text], NFAState]]
+    arcs: List[Tuple[Text | None, NFAState]]
     def __init__(self) -> None: ...
-    def addarc(self, next: NFAState, label: Optional[Text] = ...) -> None: ...
+    def addarc(self, next: NFAState, label: Text | None = ...) -> None: ...
 
 class DFAState:
     nfaset: Dict[NFAState, Any]
diff --git a/stdlib/@python2/lib2to3/pytree.pyi b/stdlib/@python2/lib2to3/pytree.pyi
index 48d11f84f201..27c64853329e 100644
--- a/stdlib/@python2/lib2to3/pytree.pyi
+++ b/stdlib/@python2/lib2to3/pytree.pyi
@@ -14,7 +14,7 @@ def type_repr(type_num: int) -> Text: ...
 
 class Base:
     type: int
-    parent: Optional[Node]
+    parent: Node | None
     prefix: Text
     children: List[_NL]
     was_changed: bool
@@ -24,14 +24,14 @@ class Base:
     def clone(self: _P) -> _P: ...
     def post_order(self) -> Iterator[_NL]: ...
     def pre_order(self) -> Iterator[_NL]: ...
-    def replace(self, new: Union[_NL, List[_NL]]) -> None: ...
+    def replace(self, new: _NL | List[_NL]) -> None: ...
     def get_lineno(self) -> int: ...
     def changed(self) -> None: ...
-    def remove(self) -> Optional[int]: ...
+    def remove(self) -> int | None: ...
     @property
-    def next_sibling(self) -> Optional[_NL]: ...
+    def next_sibling(self) -> _NL | None: ...
     @property
-    def prev_sibling(self) -> Optional[_NL]: ...
+    def prev_sibling(self) -> _NL | None: ...
     def leaves(self) -> Iterator[Leaf]: ...
     def depth(self) -> int: ...
     def get_suffix(self) -> Text: ...
@@ -44,9 +44,9 @@ class Node(Base):
         self,
         type: int,
         children: List[_NL],
-        context: Optional[Any] = ...,
-        prefix: Optional[Text] = ...,
-        fixers_applied: Optional[List[Any]] = ...,
+        context: Any | None = ...,
+        prefix: Text | None = ...,
+        fixers_applied: List[Any] | None = ...,
     ) -> None: ...
     def set_child(self, i: int, child: _NL) -> None: ...
     def insert_child(self, i: int, child: _NL) -> None: ...
@@ -58,38 +58,33 @@ class Leaf(Base):
     value: Text
     fixers_applied: List[Any]
     def __init__(
-        self,
-        type: int,
-        value: Text,
-        context: Optional[_Context] = ...,
-        prefix: Optional[Text] = ...,
-        fixers_applied: List[Any] = ...,
+        self, type: int, value: Text, context: _Context | None = ..., prefix: Text | None = ..., fixers_applied: List[Any] = ...
     ) -> None: ...
 
 def convert(gr: Grammar, raw_node: _RawNode) -> _NL: ...
 
 class BasePattern:
     type: int
-    content: Optional[Text]
-    name: Optional[Text]
+    content: Text | None
+    name: Text | None
     def optimize(self) -> BasePattern: ...  # sic, subclasses are free to optimize themselves into different patterns
-    def match(self, node: _NL, results: Optional[_Results] = ...) -> bool: ...
-    def match_seq(self, nodes: List[_NL], results: Optional[_Results] = ...) -> bool: ...
+    def match(self, node: _NL, results: _Results | None = ...) -> bool: ...
+    def match_seq(self, nodes: List[_NL], results: _Results | None = ...) -> bool: ...
     def generate_matches(self, nodes: List[_NL]) -> Iterator[Tuple[int, _Results]]: ...
 
 class LeafPattern(BasePattern):
-    def __init__(self, type: Optional[int] = ..., content: Optional[Text] = ..., name: Optional[Text] = ...) -> None: ...
+    def __init__(self, type: int | None = ..., content: Text | None = ..., name: Text | None = ...) -> None: ...
 
 class NodePattern(BasePattern):
     wildcards: bool
-    def __init__(self, type: Optional[int] = ..., content: Optional[Text] = ..., name: Optional[Text] = ...) -> None: ...
+    def __init__(self, type: int | None = ..., content: Text | None = ..., name: Text | None = ...) -> None: ...
 
 class WildcardPattern(BasePattern):
     min: int
     max: int
-    def __init__(self, content: Optional[Text] = ..., min: int = ..., max: int = ..., name: Optional[Text] = ...) -> None: ...
+    def __init__(self, content: Text | None = ..., min: int = ..., max: int = ..., name: Text | None = ...) -> None: ...
 
 class NegatedPattern(BasePattern):
-    def __init__(self, content: Optional[Text] = ...) -> None: ...
+    def __init__(self, content: Text | None = ...) -> None: ...
 
 def generate_matches(patterns: List[BasePattern], nodes: List[_NL]) -> Iterator[Tuple[int, _Results]]: ...
diff --git a/stdlib/@python2/linecache.pyi b/stdlib/@python2/linecache.pyi
index 1e5fd821b9f4..8628a0c58adc 100644
--- a/stdlib/@python2/linecache.pyi
+++ b/stdlib/@python2/linecache.pyi
@@ -1,9 +1,9 @@
-from typing import Any, Dict, List, Optional, Text
+from typing import Any, Dict, List, Text
 
 _ModuleGlobals = Dict[str, Any]
 
-def getline(filename: Text, lineno: int, module_globals: Optional[_ModuleGlobals] = ...) -> str: ...
+def getline(filename: Text, lineno: int, module_globals: _ModuleGlobals | None = ...) -> str: ...
 def clearcache() -> None: ...
-def getlines(filename: Text, module_globals: Optional[_ModuleGlobals] = ...) -> List[str]: ...
-def checkcache(filename: Optional[Text] = ...) -> None: ...
-def updatecache(filename: Text, module_globals: Optional[_ModuleGlobals] = ...) -> List[str]: ...
+def getlines(filename: Text, module_globals: _ModuleGlobals | None = ...) -> List[str]: ...
+def checkcache(filename: Text | None = ...) -> None: ...
+def updatecache(filename: Text, module_globals: _ModuleGlobals | None = ...) -> List[str]: ...
diff --git a/stdlib/@python2/locale.pyi b/stdlib/@python2/locale.pyi
index eb73dfcb62a2..21a7da166e29 100644
--- a/stdlib/@python2/locale.pyi
+++ b/stdlib/@python2/locale.pyi
@@ -1,7 +1,7 @@
 # workaround for mypy#2010
 from __builtin__ import str as _str
 from decimal import Decimal
-from typing import Any, Callable, Dict, Iterable, List, Mapping, Optional, Sequence, Tuple, Union
+from typing import Any, Callable, Dict, Iterable, List, Mapping, Sequence, Tuple
 
 CODESET: int
 D_T_FMT: int
@@ -74,19 +74,19 @@ CHAR_MAX: int
 
 class Error(Exception): ...
 
-def setlocale(category: int, locale: Union[_str, Iterable[_str], None] = ...) -> _str: ...
-def localeconv() -> Mapping[_str, Union[int, _str, List[int]]]: ...
+def setlocale(category: int, locale: _str | Iterable[_str] | None = ...) -> _str: ...
+def localeconv() -> Mapping[_str, int | _str | List[int]]: ...
 def nl_langinfo(__key: int) -> _str: ...
-def getdefaultlocale(envvars: Tuple[_str, ...] = ...) -> Tuple[Optional[_str], Optional[_str]]: ...
+def getdefaultlocale(envvars: Tuple[_str, ...] = ...) -> Tuple[_str | None, _str | None]: ...
 def getlocale(category: int = ...) -> Sequence[_str]: ...
 def getpreferredencoding(do_setlocale: bool = ...) -> _str: ...
 def normalize(localename: _str) -> _str: ...
 def resetlocale(category: int = ...) -> None: ...
 def strcoll(string1: _str, string2: _str) -> int: ...
 def strxfrm(string: _str) -> _str: ...
-def format(percent: _str, value: Union[float, Decimal], grouping: bool = ..., monetary: bool = ..., *additional: Any) -> _str: ...
+def format(percent: _str, value: float | Decimal, grouping: bool = ..., monetary: bool = ..., *additional: Any) -> _str: ...
 def format_string(f: _str, val: Any, grouping: bool = ...) -> _str: ...
-def currency(val: Union[int, float, Decimal], symbol: bool = ..., grouping: bool = ..., international: bool = ...) -> _str: ...
+def currency(val: int | float | Decimal, symbol: bool = ..., grouping: bool = ..., international: bool = ...) -> _str: ...
 def atof(string: _str, func: Callable[[_str], float] = ...) -> float: ...
 def atoi(string: _str) -> int: ...
 def str(val: float) -> _str: ...
diff --git a/stdlib/@python2/logging/__init__.pyi b/stdlib/@python2/logging/__init__.pyi
index 242132c820d5..9cca9b51f753 100644
--- a/stdlib/@python2/logging/__init__.pyi
+++ b/stdlib/@python2/logging/__init__.pyi
@@ -14,11 +14,11 @@ raiseExceptions: bool
 logThreads: bool
 logMultiprocessing: bool
 logProcesses: bool
-_srcfile: Optional[str]
+_srcfile: str | None
 
 def currentframe() -> FrameType: ...
 
-_levelNames: Dict[Union[int, str], Union[str, int]]  # Union[int:str, str:int]
+_levelNames: Dict[int | str, str | int]  # Union[int:str, str:int]
 
 class Filterer(object):
     filters: List[Filter]
@@ -30,7 +30,7 @@ class Filterer(object):
 class Logger(Filterer):
     name: str
     level: int
-    parent: Union[Logger, PlaceHolder]
+    parent: Logger | PlaceHolder
     propagate: bool
     handlers: List[Handler]
     disabled: int
@@ -40,30 +40,30 @@ class Logger(Filterer):
     def getEffectiveLevel(self) -> int: ...
     def getChild(self, suffix: str) -> Logger: ...
     def debug(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def info(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def warning(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     warn = warning
     def error(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def critical(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     fatal = critical
     def log(
-        self, level: int, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, level: int, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def exception(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def _log(
-        self, level: int, msg: Any, args: _ArgsType, exc_info: Optional[_ExcInfoType] = ..., extra: Optional[Dict[str, Any]] = ...
+        self, level: int, msg: Any, args: _ArgsType, exc_info: _ExcInfoType | None = ..., extra: Dict[str, Any] | None = ...
     ) -> None: ...  # undocumented
     def filter(self, record: LogRecord) -> bool: ...
     def addHandler(self, hdlr: Handler) -> None: ...
@@ -78,9 +78,9 @@ class Logger(Filterer):
         lno: int,
         msg: Any,
         args: _ArgsType,
-        exc_info: Optional[_SysExcInfoType],
-        func: Optional[str] = ...,
-        extra: Optional[Mapping[str, Any]] = ...,
+        exc_info: _SysExcInfoType | None,
+        func: str | None = ...,
+        extra: Mapping[str, Any] | None = ...,
     ) -> LogRecord: ...
 
 CRITICAL: int
@@ -94,9 +94,9 @@ NOTSET: int
 
 class Handler(Filterer):
     level: int  # undocumented
-    formatter: Optional[Formatter]  # undocumented
-    lock: Optional[threading.Lock]  # undocumented
-    name: Optional[str]  # undocumented
+    formatter: Formatter | None  # undocumented
+    lock: threading.Lock | None  # undocumented
+    name: str | None  # undocumented
     def __init__(self, level: _Level = ...) -> None: ...
     def createLock(self) -> None: ...
     def acquire(self) -> None: ...
@@ -112,12 +112,12 @@ class Handler(Filterer):
     def emit(self, record: LogRecord) -> None: ...
 
 class Formatter:
-    converter: Callable[[Optional[float]], struct_time]
-    _fmt: Optional[str]
-    datefmt: Optional[str]
-    def __init__(self, fmt: Optional[str] = ..., datefmt: Optional[str] = ...) -> None: ...
+    converter: Callable[[float | None], struct_time]
+    _fmt: str | None
+    datefmt: str | None
+    def __init__(self, fmt: str | None = ..., datefmt: str | None = ...) -> None: ...
     def format(self, record: LogRecord) -> str: ...
-    def formatTime(self, record: LogRecord, datefmt: Optional[str] = ...) -> str: ...
+    def formatTime(self, record: LogRecord, datefmt: str | None = ...) -> str: ...
     def formatException(self, ei: _SysExcInfoType) -> str: ...
 
 class Filter:
@@ -128,8 +128,8 @@ class LogRecord:
     args: _ArgsType
     asctime: str
     created: int
-    exc_info: Optional[_SysExcInfoType]
-    exc_text: Optional[str]
+    exc_info: _SysExcInfoType | None
+    exc_text: str | None
     filename: str
     funcName: str
     levelname: str
@@ -154,8 +154,8 @@ class LogRecord:
         lineno: int,
         msg: Any,
         args: _ArgsType,
-        exc_info: Optional[_SysExcInfoType],
-        func: Optional[str] = ...,
+        exc_info: _SysExcInfoType | None,
+        func: str | None = ...,
     ) -> None: ...
     def getMessage(self) -> str: ...
 
@@ -165,66 +165,62 @@ class LoggerAdapter:
     def __init__(self, logger: Logger, extra: Mapping[str, Any]) -> None: ...
     def process(self, msg: Any, kwargs: MutableMapping[str, Any]) -> Tuple[Any, MutableMapping[str, Any]]: ...
     def debug(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def info(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def warning(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def error(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def exception(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def critical(
-        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def log(
-        self, level: int, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+        self, level: int, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
     ) -> None: ...
     def isEnabledFor(self, level: int) -> bool: ...
 
 @overload
 def getLogger() -> Logger: ...
 @overload
-def getLogger(name: Union[Text, str]) -> Logger: ...
+def getLogger(name: Text | str) -> Logger: ...
 def getLoggerClass() -> type: ...
-def debug(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any) -> None: ...
-def info(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any) -> None: ...
-def warning(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any) -> None: ...
+def debug(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any) -> None: ...
+def info(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any) -> None: ...
+def warning(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any) -> None: ...
 
 warn = warning
 
-def error(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any) -> None: ...
-def critical(
-    msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
-) -> None: ...
-def exception(
-    msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
-) -> None: ...
+def error(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any) -> None: ...
+def critical(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any) -> None: ...
+def exception(msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any) -> None: ...
 def log(
-    level: int, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Optional[Dict[str, Any]] = ..., **kwargs: Any
+    level: int, msg: Any, *args: Any, exc_info: _ExcInfoType = ..., extra: Dict[str, Any] | None = ..., **kwargs: Any
 ) -> None: ...
 
 fatal = critical
 
 def disable(level: int) -> None: ...
 def addLevelName(level: int, levelName: str) -> None: ...
-def getLevelName(level: Union[int, str]) -> Any: ...
+def getLevelName(level: int | str) -> Any: ...
 def makeLogRecord(dict: Mapping[str, Any]) -> LogRecord: ...
 @overload
 def basicConfig() -> None: ...
 @overload
 def basicConfig(
     *,
-    filename: Optional[str] = ...,
+    filename: str | None = ...,
     filemode: str = ...,
     format: str = ...,
-    datefmt: Optional[str] = ...,
-    level: Optional[_Level] = ...,
+    datefmt: str | None = ...,
+    level: _Level | None = ...,
     stream: IO[str] = ...,
 ) -> None: ...
 def shutdown(handlerList: Sequence[Any] = ...) -> None: ...  # handlerList is undocumented
@@ -233,14 +229,14 @@ def captureWarnings(capture: bool) -> None: ...
 
 class StreamHandler(Handler):
     stream: IO[str]  # undocumented
-    def __init__(self, stream: Optional[IO[str]] = ...) -> None: ...
+    def __init__(self, stream: IO[str] | None = ...) -> None: ...
 
 class FileHandler(StreamHandler):
     baseFilename: str  # undocumented
     mode: str  # undocumented
-    encoding: Optional[str]  # undocumented
+    encoding: str | None  # undocumented
     delay: bool  # undocumented
-    def __init__(self, filename: StrPath, mode: str = ..., encoding: Optional[str] = ..., delay: bool = ...) -> None: ...
+    def __init__(self, filename: StrPath, mode: str = ..., encoding: str | None = ..., delay: bool = ...) -> None: ...
     def _open(self) -> IO[Any]: ...
 
 class NullHandler(Handler): ...
diff --git a/stdlib/@python2/logging/config.pyi b/stdlib/@python2/logging/config.pyi
index 3d8817b7736f..03707bb98f55 100644
--- a/stdlib/@python2/logging/config.pyi
+++ b/stdlib/@python2/logging/config.pyi
@@ -1,12 +1,10 @@
 from _typeshed import StrPath
 from threading import Thread
-from typing import IO, Any, Dict, Optional, Union
+from typing import IO, Any, Dict
 
 _Path = StrPath
 
 def dictConfig(config: Dict[str, Any]) -> None: ...
-def fileConfig(
-    fname: Union[str, IO[str]], defaults: Optional[Dict[str, str]] = ..., disable_existing_loggers: bool = ...
-) -> None: ...
+def fileConfig(fname: str | IO[str], defaults: Dict[str, str] | None = ..., disable_existing_loggers: bool = ...) -> None: ...
 def listen(port: int = ...) -> Thread: ...
 def stopListening() -> None: ...
diff --git a/stdlib/@python2/logging/handlers.pyi b/stdlib/@python2/logging/handlers.pyi
index ed7e6d74dd17..174c7bde3d68 100644
--- a/stdlib/@python2/logging/handlers.pyi
+++ b/stdlib/@python2/logging/handlers.pyi
@@ -1,7 +1,7 @@
 from _typeshed import StrPath
 from logging import FileHandler, Handler, LogRecord
 from socket import SocketKind, SocketType
-from typing import Any, ClassVar, Dict, List, Optional, Tuple, Union
+from typing import Any, ClassVar, Dict, List, Tuple
 
 DEFAULT_TCP_LOGGING_PORT: int
 DEFAULT_UDP_LOGGING_PORT: int
@@ -13,7 +13,7 @@ SYSLOG_TCP_PORT: int
 class WatchedFileHandler(FileHandler):
     dev: int
     ino: int
-    def __init__(self, filename: StrPath, mode: str = ..., encoding: Optional[str] = ..., delay: bool = ...) -> None: ...
+    def __init__(self, filename: StrPath, mode: str = ..., encoding: str | None = ..., delay: bool = ...) -> None: ...
     def _statstream(self) -> None: ...
 
 class RotatingFileHandler(Handler):
@@ -23,7 +23,7 @@ class RotatingFileHandler(Handler):
         mode: str = ...,
         maxBytes: int = ...,
         backupCount: int = ...,
-        encoding: Optional[str] = ...,
+        encoding: str | None = ...,
         delay: bool = ...,
     ) -> None: ...
     def doRollover(self) -> None: ...
@@ -35,7 +35,7 @@ class TimedRotatingFileHandler(Handler):
         when: str = ...,
         interval: int = ...,
         backupCount: int = ...,
-        encoding: Optional[str] = ...,
+        encoding: str | None = ...,
         delay: bool = ...,
         utc: bool = ...,
     ) -> None: ...
@@ -90,14 +90,12 @@ class SysLogHandler(Handler):
     priority_names: ClassVar[Dict[str, int]]  # undocumented
     facility_names: ClassVar[Dict[str, int]]  # undocumented
     priority_map: ClassVar[Dict[str, str]]  # undocumented
-    def __init__(
-        self, address: Union[Tuple[str, int], str] = ..., facility: int = ..., socktype: Optional[SocketKind] = ...
-    ) -> None: ...
-    def encodePriority(self, facility: Union[int, str], priority: Union[int, str]) -> int: ...
+    def __init__(self, address: Tuple[str, int] | str = ..., facility: int = ..., socktype: SocketKind | None = ...) -> None: ...
+    def encodePriority(self, facility: int | str, priority: int | str) -> int: ...
     def mapPriority(self, levelName: str) -> str: ...
 
 class NTEventLogHandler(Handler):
-    def __init__(self, appname: str, dllname: Optional[str] = ..., logtype: str = ...) -> None: ...
+    def __init__(self, appname: str, dllname: str | None = ..., logtype: str = ...) -> None: ...
     def getEventCategory(self, record: LogRecord) -> int: ...
     # TODO correct return value?
     def getEventType(self, record: LogRecord) -> int: ...
@@ -107,12 +105,12 @@ class SMTPHandler(Handler):
     # TODO `secure` can also be an empty tuple
     def __init__(
         self,
-        mailhost: Union[str, Tuple[str, int]],
+        mailhost: str | Tuple[str, int],
         fromaddr: str,
         toaddrs: List[str],
         subject: str,
-        credentials: Optional[Tuple[str, str]] = ...,
-        secure: Union[Tuple[str], Tuple[str, str], None] = ...,
+        credentials: Tuple[str, str] | None = ...,
+        secure: Tuple[str] | Tuple[str, str] | None = ...,
     ) -> None: ...
     def getSubject(self, record: LogRecord) -> str: ...
 
@@ -122,7 +120,7 @@ class BufferingHandler(Handler):
     def shouldFlush(self, record: LogRecord) -> bool: ...
 
 class MemoryHandler(BufferingHandler):
-    def __init__(self, capacity: int, flushLevel: int = ..., target: Optional[Handler] = ...) -> None: ...
+    def __init__(self, capacity: int, flushLevel: int = ..., target: Handler | None = ...) -> None: ...
     def setTarget(self, target: Handler) -> None: ...
 
 class HTTPHandler(Handler):
diff --git a/stdlib/@python2/macpath.pyi b/stdlib/@python2/macpath.pyi
index 74e3315f6481..bcb882e23eef 100644
--- a/stdlib/@python2/macpath.pyi
+++ b/stdlib/@python2/macpath.pyi
@@ -27,9 +27,9 @@ from posixpath import (
     splitext as splitext,
     supports_unicode_filenames as supports_unicode_filenames,
 )
-from typing import AnyStr, Optional, Text, Tuple, overload
+from typing import AnyStr, Text, Tuple, overload
 
-altsep: Optional[str]
+altsep: str | None
 
 def basename(s: AnyStr) -> AnyStr: ...
 def dirname(s: AnyStr) -> AnyStr: ...
diff --git a/stdlib/@python2/macurl2path.pyi b/stdlib/@python2/macurl2path.pyi
index 025820b44e89..6aac6dfeace5 100644
--- a/stdlib/@python2/macurl2path.pyi
+++ b/stdlib/@python2/macurl2path.pyi
@@ -1,5 +1,3 @@
-from typing import Union
-
 def url2pathname(pathname: str) -> str: ...
 def pathname2url(pathname: str) -> str: ...
-def _pncomp2url(component: Union[str, bytes]) -> str: ...
+def _pncomp2url(component: str | bytes) -> str: ...
diff --git a/stdlib/@python2/mailbox.pyi b/stdlib/@python2/mailbox.pyi
index 38663a391b8f..18a66fa964c4 100644
--- a/stdlib/@python2/mailbox.pyi
+++ b/stdlib/@python2/mailbox.pyi
@@ -11,7 +11,6 @@ from typing import (
     Iterator,
     List,
     Mapping,
-    Optional,
     Protocol,
     Sequence,
     Text,
@@ -37,18 +36,18 @@ linesep: bytes
 
 class Mailbox(Generic[_MessageT]):
 
-    _path: Union[bytes, str]  # undocumented
-    _factory: Optional[Callable[[IO[Any]], _MessageT]]  # undocumented
-    def __init__(self, path: Text, factory: Optional[Callable[[IO[Any]], _MessageT]] = ..., create: bool = ...) -> None: ...
+    _path: bytes | str  # undocumented
+    _factory: Callable[[IO[Any]], _MessageT] | None  # undocumented
+    def __init__(self, path: Text, factory: Callable[[IO[Any]], _MessageT] | None = ..., create: bool = ...) -> None: ...
     def add(self, message: _MessageData) -> str: ...
     def remove(self, key: str) -> None: ...
     def __delitem__(self, key: str) -> None: ...
     def discard(self, key: str) -> None: ...
     def __setitem__(self, key: str, message: _MessageData) -> None: ...
     @overload
-    def get(self, key: str, default: None = ...) -> Optional[_MessageT]: ...
+    def get(self, key: str, default: None = ...) -> _MessageT | None: ...
     @overload
-    def get(self, key: str, default: _T) -> Union[_MessageT, _T]: ...
+    def get(self, key: str, default: _T) -> _MessageT | _T: ...
     def __getitem__(self, key: str) -> _MessageT: ...
     def get_message(self, key: str) -> _MessageT: ...
     def get_string(self, key: str) -> str: ...
@@ -66,11 +65,11 @@ class Mailbox(Generic[_MessageT]):
     def __len__(self) -> int: ...
     def clear(self) -> None: ...
     @overload
-    def pop(self, key: str, default: None = ...) -> Optional[_MessageT]: ...
+    def pop(self, key: str, default: None = ...) -> _MessageT | None: ...
     @overload
-    def pop(self, key: str, default: _T = ...) -> Union[_MessageT, _T]: ...
+    def pop(self, key: str, default: _T = ...) -> _MessageT | _T: ...
     def popitem(self) -> Tuple[str, _MessageT]: ...
-    def update(self, arg: Optional[Union[_HasIteritems, _HasItems, Iterable[Tuple[str, _MessageData]]]] = ...) -> None: ...
+    def update(self, arg: _HasIteritems | _HasItems | Iterable[Tuple[str, _MessageData]] | None = ...) -> None: ...
     def flush(self) -> None: ...
     def lock(self) -> None: ...
     def unlock(self) -> None: ...
@@ -79,16 +78,14 @@ class Mailbox(Generic[_MessageT]):
 class Maildir(Mailbox[MaildirMessage]):
 
     colon: str
-    def __init__(
-        self, dirname: Text, factory: Optional[Callable[[IO[Any]], MaildirMessage]] = ..., create: bool = ...
-    ) -> None: ...
+    def __init__(self, dirname: Text, factory: Callable[[IO[Any]], MaildirMessage] | None = ..., create: bool = ...) -> None: ...
     def get_file(self, key: str) -> _ProxyFile[bytes]: ...
     def list_folders(self) -> List[str]: ...
     def get_folder(self, folder: Text) -> Maildir: ...
     def add_folder(self, folder: Text) -> Maildir: ...
     def remove_folder(self, folder: Text) -> None: ...
     def clean(self) -> None: ...
-    def next(self) -> Optional[str]: ...
+    def next(self) -> str | None: ...
 
 class _singlefileMailbox(Mailbox[_MessageT]): ...
 
@@ -98,13 +95,13 @@ class _mboxMMDF(_singlefileMailbox[_MessageT]):
     def get_string(self, key: str, from_: bool = ...) -> str: ...
 
 class mbox(_mboxMMDF[mboxMessage]):
-    def __init__(self, path: Text, factory: Optional[Callable[[IO[Any]], mboxMessage]] = ..., create: bool = ...) -> None: ...
+    def __init__(self, path: Text, factory: Callable[[IO[Any]], mboxMessage] | None = ..., create: bool = ...) -> None: ...
 
 class MMDF(_mboxMMDF[MMDFMessage]):
-    def __init__(self, path: Text, factory: Optional[Callable[[IO[Any]], MMDFMessage]] = ..., create: bool = ...) -> None: ...
+    def __init__(self, path: Text, factory: Callable[[IO[Any]], MMDFMessage] | None = ..., create: bool = ...) -> None: ...
 
 class MH(Mailbox[MHMessage]):
-    def __init__(self, path: Text, factory: Optional[Callable[[IO[Any]], MHMessage]] = ..., create: bool = ...) -> None: ...
+    def __init__(self, path: Text, factory: Callable[[IO[Any]], MHMessage] | None = ..., create: bool = ...) -> None: ...
     def get_file(self, key: str) -> _ProxyFile[bytes]: ...
     def list_folders(self) -> List[str]: ...
     def get_folder(self, folder: Text) -> MH: ...
@@ -115,12 +112,12 @@ class MH(Mailbox[MHMessage]):
     def pack(self) -> None: ...
 
 class Babyl(_singlefileMailbox[BabylMessage]):
-    def __init__(self, path: Text, factory: Optional[Callable[[IO[Any]], BabylMessage]] = ..., create: bool = ...) -> None: ...
+    def __init__(self, path: Text, factory: Callable[[IO[Any]], BabylMessage] | None = ..., create: bool = ...) -> None: ...
     def get_file(self, key: str) -> IO[bytes]: ...
     def get_labels(self) -> List[str]: ...
 
 class Message(email.message.Message):
-    def __init__(self, message: Optional[_MessageData] = ...) -> None: ...
+    def __init__(self, message: _MessageData | None = ...) -> None: ...
 
 class MaildirMessage(Message):
     def get_subdir(self) -> str: ...
@@ -136,9 +133,7 @@ class MaildirMessage(Message):
 
 class _mboxMMDFMessage(Message):
     def get_from(self) -> str: ...
-    def set_from(
-        self, from_: str, time_: Optional[Union[bool, Tuple[int, int, int, int, int, int, int, int, int]]] = ...
-    ) -> None: ...
+    def set_from(self, from_: str, time_: bool | Tuple[int, int, int, int, int, int, int, int, int] | None = ...) -> None: ...
     def get_flags(self) -> str: ...
     def set_flags(self, flags: Iterable[str]) -> None: ...
     def add_flag(self, flag: str) -> None: ...
@@ -164,19 +159,17 @@ class BabylMessage(Message):
 class MMDFMessage(_mboxMMDFMessage): ...
 
 class _ProxyFile(Generic[AnyStr]):
-    def __init__(self, f: IO[AnyStr], pos: Optional[int] = ...) -> None: ...
-    def read(self, size: Optional[int] = ...) -> AnyStr: ...
-    def read1(self, size: Optional[int] = ...) -> AnyStr: ...
-    def readline(self, size: Optional[int] = ...) -> AnyStr: ...
-    def readlines(self, sizehint: Optional[int] = ...) -> List[AnyStr]: ...
+    def __init__(self, f: IO[AnyStr], pos: int | None = ...) -> None: ...
+    def read(self, size: int | None = ...) -> AnyStr: ...
+    def read1(self, size: int | None = ...) -> AnyStr: ...
+    def readline(self, size: int | None = ...) -> AnyStr: ...
+    def readlines(self, sizehint: int | None = ...) -> List[AnyStr]: ...
     def __iter__(self) -> Iterator[AnyStr]: ...
     def tell(self) -> int: ...
     def seek(self, offset: int, whence: int = ...) -> None: ...
     def close(self) -> None: ...
     def __enter__(self) -> _ProxyFile[AnyStr]: ...
-    def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc: Optional[BaseException], tb: Optional[TracebackType]
-    ) -> None: ...
+    def __exit__(self, exc_type: Type[BaseException] | None, exc: BaseException | None, tb: TracebackType | None) -> None: ...
     def readable(self) -> bool: ...
     def writable(self) -> bool: ...
     def seekable(self) -> bool: ...
@@ -185,7 +178,7 @@ class _ProxyFile(Generic[AnyStr]):
     def closed(self) -> bool: ...
 
 class _PartialFile(_ProxyFile[AnyStr]):
-    def __init__(self, f: IO[AnyStr], start: Optional[int] = ..., stop: Optional[int] = ...) -> None: ...
+    def __init__(self, f: IO[AnyStr], start: int | None = ..., stop: int | None = ...) -> None: ...
 
 class Error(Exception): ...
 class NoSuchMailboxError(Error): ...
diff --git a/stdlib/@python2/mailcap.pyi b/stdlib/@python2/mailcap.pyi
index a65cc3a329d3..b29854f3c744 100644
--- a/stdlib/@python2/mailcap.pyi
+++ b/stdlib/@python2/mailcap.pyi
@@ -1,8 +1,8 @@
-from typing import Dict, List, Mapping, Optional, Sequence, Tuple, Union
+from typing import Dict, List, Mapping, Sequence, Tuple, Union
 
 _Cap = Dict[str, Union[str, int]]
 
 def findmatch(
     caps: Mapping[str, List[_Cap]], MIMEtype: str, key: str = ..., filename: str = ..., plist: Sequence[str] = ...
-) -> Tuple[Optional[str], Optional[_Cap]]: ...
+) -> Tuple[str | None, _Cap | None]: ...
 def getcaps() -> Dict[str, List[_Cap]]: ...
diff --git a/stdlib/@python2/mimetypes.pyi b/stdlib/@python2/mimetypes.pyi
index 5412a5c7c21b..a9661dab56ad 100644
--- a/stdlib/@python2/mimetypes.pyi
+++ b/stdlib/@python2/mimetypes.pyi
@@ -1,11 +1,11 @@
 import sys
-from typing import IO, Dict, List, Optional, Sequence, Text, Tuple
+from typing import IO, Dict, List, Sequence, Text, Tuple
 
-def guess_type(url: Text, strict: bool = ...) -> Tuple[Optional[str], Optional[str]]: ...
+def guess_type(url: Text, strict: bool = ...) -> Tuple[str | None, str | None]: ...
 def guess_all_extensions(type: str, strict: bool = ...) -> List[str]: ...
-def guess_extension(type: str, strict: bool = ...) -> Optional[str]: ...
-def init(files: Optional[Sequence[str]] = ...) -> None: ...
-def read_mime_types(file: str) -> Optional[Dict[str, str]]: ...
+def guess_extension(type: str, strict: bool = ...) -> str | None: ...
+def init(files: Sequence[str] | None = ...) -> None: ...
+def read_mime_types(file: str) -> Dict[str, str] | None: ...
 def add_type(type: str, ext: str, strict: bool = ...) -> None: ...
 
 inited: bool
@@ -21,8 +21,8 @@ class MimeTypes:
     types_map: Tuple[Dict[str, str], Dict[str, str]]
     types_map_inv: Tuple[Dict[str, str], Dict[str, str]]
     def __init__(self, filenames: Tuple[str, ...] = ..., strict: bool = ...) -> None: ...
-    def guess_extension(self, type: str, strict: bool = ...) -> Optional[str]: ...
-    def guess_type(self, url: str, strict: bool = ...) -> Tuple[Optional[str], Optional[str]]: ...
+    def guess_extension(self, type: str, strict: bool = ...) -> str | None: ...
+    def guess_type(self, url: str, strict: bool = ...) -> Tuple[str | None, str | None]: ...
     def guess_all_extensions(self, type: str, strict: bool = ...) -> List[str]: ...
     def read(self, filename: str, strict: bool = ...) -> None: ...
     def readfp(self, fp: IO[str], strict: bool = ...) -> None: ...
diff --git a/stdlib/@python2/mmap.pyi b/stdlib/@python2/mmap.pyi
index 750d0829cb8f..44369e6c051d 100644
--- a/stdlib/@python2/mmap.pyi
+++ b/stdlib/@python2/mmap.pyi
@@ -1,5 +1,5 @@
 import sys
-from typing import NoReturn, Optional, Sequence, Union
+from typing import NoReturn, Sequence
 
 ACCESS_DEFAULT: int
 ACCESS_READ: int
@@ -25,9 +25,7 @@ if sys.platform != "win32":
 
 class mmap(Sequence[bytes]):
     if sys.platform == "win32":
-        def __init__(
-            self, fileno: int, length: int, tagname: Optional[str] = ..., access: int = ..., offset: int = ...
-        ) -> None: ...
+        def __init__(self, fileno: int, length: int, tagname: str | None = ..., access: int = ..., offset: int = ...) -> None: ...
     else:
         def __init__(
             self, fileno: int, length: int, flags: int = ..., prot: int = ..., access: int = ..., offset: int = ...
@@ -47,7 +45,7 @@ class mmap(Sequence[bytes]):
     def rfind(self, string: bytes, start: int = ..., stop: int = ...) -> int: ...
     def read(self, num: int) -> bytes: ...
     def write(self, string: bytes) -> None: ...
-    def __getitem__(self, index: Union[int, slice]) -> bytes: ...
-    def __getslice__(self, i: Optional[int], j: Optional[int]) -> bytes: ...
-    def __delitem__(self, index: Union[int, slice]) -> NoReturn: ...
-    def __setitem__(self, index: Union[int, slice], object: bytes) -> None: ...
+    def __getitem__(self, index: int | slice) -> bytes: ...
+    def __getslice__(self, i: int | None, j: int | None) -> bytes: ...
+    def __delitem__(self, index: int | slice) -> NoReturn: ...
+    def __setitem__(self, index: int | slice, object: bytes) -> None: ...
diff --git a/stdlib/@python2/modulefinder.pyi b/stdlib/@python2/modulefinder.pyi
index 6fb953242b72..76fd014daf6e 100644
--- a/stdlib/@python2/modulefinder.pyi
+++ b/stdlib/@python2/modulefinder.pyi
@@ -1,5 +1,5 @@
 from types import CodeType
-from typing import IO, Any, Container, Dict, Iterable, List, Optional, Sequence, Tuple
+from typing import IO, Any, Container, Dict, Iterable, List, Sequence, Tuple
 
 LOAD_CONST: int  # undocumented
 IMPORT_NAME: int  # undocumented
@@ -17,7 +17,7 @@ replacePackageMap: Dict[str, str]  # undocumented
 def ReplacePackage(oldname: str, newname: str) -> None: ...
 
 class Module:  # undocumented
-    def __init__(self, name: str, file: Optional[str] = ..., path: Optional[str] = ...) -> None: ...
+    def __init__(self, name: str, file: str | None = ..., path: str | None = ...) -> None: ...
     def __repr__(self) -> str: ...
 
 class ModuleFinder:
@@ -31,7 +31,7 @@ class ModuleFinder:
     replace_paths: Sequence[Tuple[str, str]]  # undocumented
     def __init__(
         self,
-        path: Optional[List[str]] = ...,
+        path: List[str] | None = ...,
         debug: int = ...,
         excludes: Container[str] = ...,
         replace_paths: Sequence[Tuple[str, str]] = ...,
@@ -42,21 +42,21 @@ class ModuleFinder:
     def run_script(self, pathname: str) -> None: ...
     def load_file(self, pathname: str) -> None: ...  # undocumented
     def import_hook(
-        self, name: str, caller: Optional[Module] = ..., fromlist: Optional[List[str]] = ..., level: int = ...
-    ) -> Optional[Module]: ...  # undocumented
-    def determine_parent(self, caller: Optional[Module], level: int = ...) -> Optional[Module]: ...  # undocumented
+        self, name: str, caller: Module | None = ..., fromlist: List[str] | None = ..., level: int = ...
+    ) -> Module | None: ...  # undocumented
+    def determine_parent(self, caller: Module | None, level: int = ...) -> Module | None: ...  # undocumented
     def find_head_package(self, parent: Module, name: str) -> Tuple[Module, str]: ...  # undocumented
     def load_tail(self, q: Module, tail: str) -> Module: ...  # undocumented
     def ensure_fromlist(self, m: Module, fromlist: Iterable[str], recursive: int = ...) -> None: ...  # undocumented
     def find_all_submodules(self, m: Module) -> Iterable[str]: ...  # undocumented
-    def import_module(self, partname: str, fqname: str, parent: Module) -> Optional[Module]: ...  # undocumented
+    def import_module(self, partname: str, fqname: str, parent: Module) -> Module | None: ...  # undocumented
     def load_module(self, fqname: str, fp: IO[str], pathname: str, file_info: Tuple[str, str, str]) -> Module: ...  # undocumented
     def scan_code(self, co: CodeType, m: Module) -> None: ...  # undocumented
     def load_package(self, fqname: str, pathname: str) -> Module: ...  # undocumented
     def add_module(self, fqname: str) -> Module: ...  # undocumented
     def find_module(
-        self, name: str, path: Optional[str], parent: Optional[Module] = ...
-    ) -> Tuple[Optional[IO[Any]], Optional[str], Tuple[str, str, int]]: ...  # undocumented
+        self, name: str, path: str | None, parent: Module | None = ...
+    ) -> Tuple[IO[Any] | None, str | None, Tuple[str, str, int]]: ...  # undocumented
     def report(self) -> None: ...
     def any_missing(self) -> List[str]: ...  # undocumented
     def any_missing_maybe(self) -> Tuple[List[str], List[str]]: ...  # undocumented
diff --git a/stdlib/@python2/msilib/__init__.pyi b/stdlib/@python2/msilib/__init__.pyi
index c783493f315e..fa6757696845 100644
--- a/stdlib/@python2/msilib/__init__.pyi
+++ b/stdlib/@python2/msilib/__init__.pyi
@@ -1,6 +1,6 @@
 import sys
 from types import ModuleType
-from typing import Any, Container, Dict, Iterable, List, Optional, Sequence, Set, Tuple, Type, Union
+from typing import Any, Container, Dict, Iterable, List, Sequence, Set, Tuple, Type
 from typing_extensions import Literal
 
 if sys.platform == "win32":
@@ -31,10 +31,10 @@ if sys.platform == "win32":
         def create(self, db: _Database) -> None: ...
     class _Unspecified: ...
     def change_sequence(
-        seq: Sequence[Tuple[str, Optional[str], int]],
+        seq: Sequence[Tuple[str, str | None, int]],
         action: str,
-        seqno: Union[int, Type[_Unspecified]] = ...,
-        cond: Union[str, Type[_Unspecified]] = ...,
+        seqno: int | Type[_Unspecified] = ...,
+        cond: str | Type[_Unspecified] = ...,
     ) -> None: ...
     def add_data(db: _Database, table: str, values: Iterable[Tuple[Any, ...]]) -> None: ...
     def add_stream(db: _Database, name: str, path: str) -> None: ...
@@ -62,11 +62,11 @@ if sys.platform == "win32":
         basedir: str
         physical: str
         logical: str
-        component: Optional[str]
+        component: str | None
         short_names: Set[str]
         ids: Set[str]
         keyfiles: Dict[str, str]
-        componentflags: Optional[int]
+        componentflags: int | None
         absolute: str
         def __init__(
             self,
@@ -76,21 +76,19 @@ if sys.platform == "win32":
             physical: str,
             _logical: str,
             default: str,
-            componentflags: Optional[int] = ...,
+            componentflags: int | None = ...,
         ) -> None: ...
         def start_component(
             self,
-            component: Optional[str] = ...,
-            feature: Optional[Feature] = ...,
-            flags: Optional[int] = ...,
-            keyfile: Optional[str] = ...,
-            uuid: Optional[str] = ...,
+            component: str | None = ...,
+            feature: Feature | None = ...,
+            flags: int | None = ...,
+            keyfile: str | None = ...,
+            uuid: str | None = ...,
         ) -> None: ...
         def make_short(self, file: str) -> str: ...
-        def add_file(
-            self, file: str, src: Optional[str] = ..., version: Optional[str] = ..., language: Optional[str] = ...
-        ) -> str: ...
-        def glob(self, pattern: str, exclude: Optional[Container[str]] = ...) -> List[str]: ...
+        def add_file(self, file: str, src: str | None = ..., version: str | None = ..., language: str | None = ...) -> str: ...
+        def glob(self, pattern: str, exclude: Container[str] | None = ...) -> List[str]: ...
         def remove_pyc(self) -> None: ...
     class Binary:
 
@@ -108,8 +106,8 @@ if sys.platform == "win32":
             desc: str,
             display: int,
             level: int = ...,
-            parent: Optional[Feature] = ...,
-            directory: Optional[str] = ...,
+            parent: Feature | None = ...,
+            directory: str | None = ...,
             attributes: int = ...,
         ) -> None: ...
         def set_current(self) -> None: ...
@@ -118,7 +116,7 @@ if sys.platform == "win32":
         dlg: Dialog
         name: str
         def __init__(self, dlg: Dialog, name: str) -> None: ...
-        def event(self, event: str, argument: str, condition: str = ..., ordering: Optional[int] = ...) -> None: ...
+        def event(self, event: str, argument: str, condition: str = ..., ordering: int | None = ...) -> None: ...
         def mapping(self, event: str, attribute: str) -> None: ...
         def condition(self, action: str, condition: str) -> None: ...
     class RadioButtonGroup(Control):
@@ -126,7 +124,7 @@ if sys.platform == "win32":
         property: str
         index: int
         def __init__(self, dlg: Dialog, name: str, property: str) -> None: ...
-        def add(self, name: str, x: int, y: int, w: int, h: int, text: str, value: Optional[str] = ...) -> None: ...
+        def add(self, name: str, x: int, y: int, w: int, h: int, text: str, value: str | None = ...) -> None: ...
     class Dialog:
 
         db: _Database
@@ -158,38 +156,20 @@ if sys.platform == "win32":
             w: int,
             h: int,
             attr: int,
-            prop: Optional[str],
-            text: Optional[str],
-            next: Optional[str],
-            help: Optional[str],
+            prop: str | None,
+            text: str | None,
+            next: str | None,
+            help: str | None,
         ) -> Control: ...
-        def text(self, name: str, x: int, y: int, w: int, h: int, attr: int, text: Optional[str]) -> Control: ...
-        def bitmap(self, name: str, x: int, y: int, w: int, h: int, text: Optional[str]) -> Control: ...
+        def text(self, name: str, x: int, y: int, w: int, h: int, attr: int, text: str | None) -> Control: ...
+        def bitmap(self, name: str, x: int, y: int, w: int, h: int, text: str | None) -> Control: ...
         def line(self, name: str, x: int, y: int, w: int, h: int) -> Control: ...
         def pushbutton(
-            self, name: str, x: int, y: int, w: int, h: int, attr: int, text: Optional[str], next: Optional[str]
+            self, name: str, x: int, y: int, w: int, h: int, attr: int, text: str | None, next: str | None
         ) -> Control: ...
         def radiogroup(
-            self,
-            name: str,
-            x: int,
-            y: int,
-            w: int,
-            h: int,
-            attr: int,
-            prop: Optional[str],
-            text: Optional[str],
-            next: Optional[str],
+            self, name: str, x: int, y: int, w: int, h: int, attr: int, prop: str | None, text: str | None, next: str | None
         ) -> RadioButtonGroup: ...
         def checkbox(
-            self,
-            name: str,
-            x: int,
-            y: int,
-            w: int,
-            h: int,
-            attr: int,
-            prop: Optional[str],
-            text: Optional[str],
-            next: Optional[str],
+            self, name: str, x: int, y: int, w: int, h: int, attr: int, prop: str | None, text: str | None, next: str | None
         ) -> Control: ...
diff --git a/stdlib/@python2/msilib/schema.pyi b/stdlib/@python2/msilib/schema.pyi
index 10b65088cf80..d59e9767c3de 100644
--- a/stdlib/@python2/msilib/schema.pyi
+++ b/stdlib/@python2/msilib/schema.pyi
@@ -1,5 +1,5 @@
 import sys
-from typing import List, Optional, Tuple
+from typing import List, Tuple
 
 if sys.platform == "win32":
     from . import Table
@@ -92,6 +92,4 @@ if sys.platform == "win32":
 
     tables: List[Table]
 
-    _Validation_records: List[
-        Tuple[str, str, str, Optional[int], Optional[int], Optional[str], Optional[int], Optional[str], Optional[str], str]
-    ]
+    _Validation_records: List[Tuple[str, str, str, int | None, int | None, str | None, int | None, str | None, str | None, str]]
diff --git a/stdlib/@python2/msilib/text.pyi b/stdlib/@python2/msilib/text.pyi
index e338b8b5ba3d..4ae8ee68184b 100644
--- a/stdlib/@python2/msilib/text.pyi
+++ b/stdlib/@python2/msilib/text.pyi
@@ -1,9 +1,9 @@
 import sys
-from typing import List, Optional, Tuple
+from typing import List, Tuple
 
 if sys.platform == "win32":
 
-    ActionText: List[Tuple[str, str, Optional[str]]]
-    UIText: List[Tuple[str, Optional[str]]]
+    ActionText: List[Tuple[str, str, str | None]]
+    UIText: List[Tuple[str, str | None]]
 
     tables: List[str]
diff --git a/stdlib/@python2/multiprocessing/__init__.pyi b/stdlib/@python2/multiprocessing/__init__.pyi
index b4f58920f574..e22e09000de1 100644
--- a/stdlib/@python2/multiprocessing/__init__.pyi
+++ b/stdlib/@python2/multiprocessing/__init__.pyi
@@ -2,7 +2,7 @@ from multiprocessing import pool
 from multiprocessing.process import Process as Process, active_children as active_children, current_process as current_process
 from multiprocessing.util import SUBDEBUG as SUBDEBUG, SUBWARNING as SUBWARNING
 from Queue import Queue as _BaseQueue
-from typing import Any, Callable, Iterable, Optional, TypeVar
+from typing import Any, Callable, Iterable, TypeVar
 
 class ProcessError(Exception): ...
 class BufferTooShort(ProcessError): ...
@@ -13,8 +13,8 @@ _T = TypeVar("_T")
 
 class Queue(_BaseQueue[_T]):
     def __init__(self, maxsize: int = ...) -> None: ...
-    def get(self, block: bool = ..., timeout: Optional[float] = ...) -> _T: ...
-    def put(self, item: _T, block: bool = ..., timeout: Optional[float] = ...) -> None: ...
+    def get(self, block: bool = ..., timeout: float | None = ...) -> _T: ...
+    def put(self, item: _T, block: bool = ..., timeout: float | None = ...) -> None: ...
     def qsize(self) -> int: ...
     def empty(self) -> bool: ...
     def full(self) -> bool: ...
@@ -29,11 +29,11 @@ def Pipe(duplex: bool = ...): ...
 def cpu_count() -> int: ...
 def freeze_support(): ...
 def get_logger(): ...
-def log_to_stderr(level: Optional[Any] = ...): ...
+def log_to_stderr(level: Any | None = ...): ...
 def allow_connection_pickling(): ...
 def Lock(): ...
 def RLock(): ...
-def Condition(lock: Optional[Any] = ...): ...
+def Condition(lock: Any | None = ...): ...
 def Semaphore(value: int = ...): ...
 def BoundedSemaphore(value: int = ...): ...
 def Event(): ...
@@ -43,8 +43,8 @@ def RawArray(typecode_or_type, size_or_initializer): ...
 def Value(typecode_or_type, *args, **kwds): ...
 def Array(typecode_or_type, size_or_initializer, **kwds): ...
 def Pool(
-    processes: Optional[int] = ...,
-    initializer: Optional[Callable[..., Any]] = ...,
+    processes: int | None = ...,
+    initializer: Callable[..., Any] | None = ...,
     initargs: Iterable[Any] = ...,
-    maxtasksperchild: Optional[int] = ...,
+    maxtasksperchild: int | None = ...,
 ) -> pool.Pool: ...
diff --git a/stdlib/@python2/multiprocessing/dummy/__init__.pyi b/stdlib/@python2/multiprocessing/dummy/__init__.pyi
index dd0b5f5246b7..80a1456d1be8 100644
--- a/stdlib/@python2/multiprocessing/dummy/__init__.pyi
+++ b/stdlib/@python2/multiprocessing/dummy/__init__.pyi
@@ -2,7 +2,7 @@ import array
 import threading
 import weakref
 from Queue import Queue
-from typing import Any, List, Optional
+from typing import Any, List
 
 class DummyProcess(threading.Thread):
     _children: weakref.WeakKeyDictionary[Any, Any]
@@ -11,7 +11,7 @@ class DummyProcess(threading.Thread):
     _start_called: bool
     def __init__(self, group=..., target=..., name=..., args=..., kwargs=...) -> None: ...
     @property
-    def exitcode(self) -> Optional[int]: ...
+    def exitcode(self) -> int | None: ...
 
 Process = DummyProcess
 
diff --git a/stdlib/@python2/multiprocessing/dummy/connection.pyi b/stdlib/@python2/multiprocessing/dummy/connection.pyi
index 73789028611e..ae5e05e9ccdd 100644
--- a/stdlib/@python2/multiprocessing/dummy/connection.pyi
+++ b/stdlib/@python2/multiprocessing/dummy/connection.pyi
@@ -1,5 +1,5 @@
 from Queue import Queue
-from typing import Any, List, Optional, Tuple
+from typing import Any, List, Tuple
 
 families: List[None]
 
@@ -15,7 +15,7 @@ class Connection(object):
     def poll(self, timeout=...) -> Any: ...
 
 class Listener(object):
-    _backlog_queue: Optional[Queue[Any]]
+    _backlog_queue: Queue[Any] | None
     address: Any
     def __init__(self, address=..., family=..., backlog=...) -> None: ...
     def accept(self) -> Connection: ...
diff --git a/stdlib/@python2/multiprocessing/pool.pyi b/stdlib/@python2/multiprocessing/pool.pyi
index b20618ca0291..be9747e89c2f 100644
--- a/stdlib/@python2/multiprocessing/pool.pyi
+++ b/stdlib/@python2/multiprocessing/pool.pyi
@@ -1,26 +1,26 @@
-from typing import Any, Callable, Dict, Iterable, Iterator, List, Optional, TypeVar
+from typing import Any, Callable, Dict, Iterable, Iterator, List, TypeVar
 
 _T = TypeVar("_T", bound=Pool)
 
 class AsyncResult:
-    def get(self, timeout: Optional[float] = ...) -> Any: ...
-    def wait(self, timeout: Optional[float] = ...) -> None: ...
+    def get(self, timeout: float | None = ...) -> Any: ...
+    def wait(self, timeout: float | None = ...) -> None: ...
     def ready(self) -> bool: ...
     def successful(self) -> bool: ...
 
 class IMapIterator(Iterator[Any]):
     def __iter__(self) -> Iterator[Any]: ...
-    def next(self, timeout: Optional[float] = ...) -> Any: ...
+    def next(self, timeout: float | None = ...) -> Any: ...
 
 class IMapUnorderedIterator(IMapIterator): ...
 
 class Pool(object):
     def __init__(
         self,
-        processes: Optional[int] = ...,
-        initializer: Optional[Callable[..., None]] = ...,
+        processes: int | None = ...,
+        initializer: Callable[..., None] | None = ...,
         initargs: Iterable[Any] = ...,
-        maxtasksperchild: Optional[int] = ...,
+        maxtasksperchild: int | None = ...,
     ) -> None: ...
     def apply(self, func: Callable[..., Any], args: Iterable[Any] = ..., kwds: Dict[str, Any] = ...) -> Any: ...
     def apply_async(
@@ -28,19 +28,19 @@ class Pool(object):
         func: Callable[..., Any],
         args: Iterable[Any] = ...,
         kwds: Dict[str, Any] = ...,
-        callback: Optional[Callable[..., None]] = ...,
+        callback: Callable[..., None] | None = ...,
     ) -> AsyncResult: ...
-    def map(self, func: Callable[..., Any], iterable: Iterable[Any] = ..., chunksize: Optional[int] = ...) -> List[Any]: ...
+    def map(self, func: Callable[..., Any], iterable: Iterable[Any] = ..., chunksize: int | None = ...) -> List[Any]: ...
     def map_async(
         self,
         func: Callable[..., Any],
         iterable: Iterable[Any] = ...,
-        chunksize: Optional[int] = ...,
-        callback: Optional[Callable[..., None]] = ...,
+        chunksize: int | None = ...,
+        callback: Callable[..., None] | None = ...,
     ) -> AsyncResult: ...
-    def imap(self, func: Callable[..., Any], iterable: Iterable[Any] = ..., chunksize: Optional[int] = ...) -> IMapIterator: ...
+    def imap(self, func: Callable[..., Any], iterable: Iterable[Any] = ..., chunksize: int | None = ...) -> IMapIterator: ...
     def imap_unordered(
-        self, func: Callable[..., Any], iterable: Iterable[Any] = ..., chunksize: Optional[int] = ...
+        self, func: Callable[..., Any], iterable: Iterable[Any] = ..., chunksize: int | None = ...
     ) -> IMapIterator: ...
     def close(self) -> None: ...
     def terminate(self) -> None: ...
@@ -48,5 +48,5 @@ class Pool(object):
 
 class ThreadPool(Pool):
     def __init__(
-        self, processes: Optional[int] = ..., initializer: Optional[Callable[..., Any]] = ..., initargs: Iterable[Any] = ...
+        self, processes: int | None = ..., initializer: Callable[..., Any] | None = ..., initargs: Iterable[Any] = ...
     ) -> None: ...
diff --git a/stdlib/@python2/multiprocessing/process.pyi b/stdlib/@python2/multiprocessing/process.pyi
index 9ab9628e0e32..2cb691342580 100644
--- a/stdlib/@python2/multiprocessing/process.pyi
+++ b/stdlib/@python2/multiprocessing/process.pyi
@@ -1,16 +1,14 @@
-from typing import Any, Optional
+from typing import Any
 
 def current_process(): ...
 def active_children(): ...
 
 class Process:
-    def __init__(
-        self, group: Optional[Any] = ..., target: Optional[Any] = ..., name: Optional[Any] = ..., args=..., kwargs=...
-    ): ...
+    def __init__(self, group: Any | None = ..., target: Any | None = ..., name: Any | None = ..., args=..., kwargs=...): ...
     def run(self): ...
     def start(self): ...
     def terminate(self): ...
-    def join(self, timeout: Optional[Any] = ...): ...
+    def join(self, timeout: Any | None = ...): ...
     def is_alive(self): ...
     @property
     def name(self): ...
diff --git a/stdlib/@python2/multiprocessing/util.pyi b/stdlib/@python2/multiprocessing/util.pyi
index 9520022e2962..6976bc3e6cf4 100644
--- a/stdlib/@python2/multiprocessing/util.pyi
+++ b/stdlib/@python2/multiprocessing/util.pyi
@@ -1,5 +1,5 @@
 import threading
-from typing import Any, Optional
+from typing import Any
 
 SUBDEBUG: Any
 SUBWARNING: Any
@@ -9,13 +9,13 @@ def debug(msg, *args): ...
 def info(msg, *args): ...
 def sub_warning(msg, *args): ...
 def get_logger(): ...
-def log_to_stderr(level: Optional[Any] = ...): ...
+def log_to_stderr(level: Any | None = ...): ...
 def get_temp_dir(): ...
 def register_after_fork(obj, func): ...
 
 class Finalize:
-    def __init__(self, obj, callback, args=..., kwargs: Optional[Any] = ..., exitpriority: Optional[Any] = ...): ...
-    def __call__(self, wr: Optional[Any] = ...): ...
+    def __init__(self, obj, callback, args=..., kwargs: Any | None = ..., exitpriority: Any | None = ...): ...
+    def __call__(self, wr: Any | None = ...): ...
     def cancel(self): ...
     def still_active(self): ...
 
diff --git a/stdlib/@python2/netrc.pyi b/stdlib/@python2/netrc.pyi
index 2ee3c522516a..3033c2f78955 100644
--- a/stdlib/@python2/netrc.pyi
+++ b/stdlib/@python2/netrc.pyi
@@ -1,10 +1,10 @@
 from typing import Dict, List, Optional, Text, Tuple
 
 class NetrcParseError(Exception):
-    filename: Optional[str]
-    lineno: Optional[int]
+    filename: str | None
+    lineno: int | None
     msg: str
-    def __init__(self, msg: str, filename: Optional[Text] = ..., lineno: Optional[int] = ...) -> None: ...
+    def __init__(self, msg: str, filename: Text | None = ..., lineno: int | None = ...) -> None: ...
 
 # (login, account, password) tuple
 _NetrcTuple = Tuple[str, Optional[str], Optional[str]]
@@ -12,5 +12,5 @@ _NetrcTuple = Tuple[str, Optional[str], Optional[str]]
 class netrc:
     hosts: Dict[str, _NetrcTuple]
     macros: Dict[str, List[str]]
-    def __init__(self, file: Optional[Text] = ...) -> None: ...
-    def authenticators(self, host: str) -> Optional[_NetrcTuple]: ...
+    def __init__(self, file: Text | None = ...) -> None: ...
+    def authenticators(self, host: str) -> _NetrcTuple | None: ...
diff --git a/stdlib/@python2/nntplib.pyi b/stdlib/@python2/nntplib.pyi
index 21b33f55d051..56545d3b88b4 100644
--- a/stdlib/@python2/nntplib.pyi
+++ b/stdlib/@python2/nntplib.pyi
@@ -1,7 +1,7 @@
 import datetime
 import socket
 import ssl
-from typing import IO, Any, Dict, Iterable, List, NamedTuple, Optional, Tuple, TypeVar, Union
+from typing import IO, Any, Dict, Iterable, List, NamedTuple, Tuple, TypeVar, Union
 
 _SelfT = TypeVar("_SelfT", bound=_NNTPBase)
 _File = Union[IO[bytes], bytes, str, None]
@@ -44,7 +44,7 @@ class _NNTPBase:
     authenticated: bool
     nntp_implementation: str
     nntp_version: int
-    def __init__(self, file: IO[bytes], host: str, readermode: Optional[bool] = ..., timeout: float = ...) -> None: ...
+    def __init__(self, file: IO[bytes], host: str, readermode: bool | None = ..., timeout: float = ...) -> None: ...
     def __enter__(self: _SelfT) -> _SelfT: ...
     def __exit__(self, *args: Any) -> None: ...
     def getwelcome(self) -> str: ...
@@ -52,11 +52,9 @@ class _NNTPBase:
     def set_debuglevel(self, level: int) -> None: ...
     def debug(self, level: int) -> None: ...
     def capabilities(self) -> Tuple[str, Dict[str, List[str]]]: ...
-    def newgroups(self, date: Union[datetime.date, datetime.datetime], *, file: _File = ...) -> Tuple[str, List[str]]: ...
-    def newnews(
-        self, group: str, date: Union[datetime.date, datetime.datetime], *, file: _File = ...
-    ) -> Tuple[str, List[str]]: ...
-    def list(self, group_pattern: Optional[str] = ..., *, file: _File = ...) -> Tuple[str, List[str]]: ...
+    def newgroups(self, date: datetime.date | datetime.datetime, *, file: _File = ...) -> Tuple[str, List[str]]: ...
+    def newnews(self, group: str, date: datetime.date | datetime.datetime, *, file: _File = ...) -> Tuple[str, List[str]]: ...
+    def list(self, group_pattern: str | None = ..., *, file: _File = ...) -> Tuple[str, List[str]]: ...
     def description(self, group: str) -> str: ...
     def descriptions(self, group_pattern: str) -> Tuple[str, Dict[str, str]]: ...
     def group(self, name: str) -> Tuple[str, int, int, int, str]: ...
@@ -71,16 +69,16 @@ class _NNTPBase:
     def xhdr(self, hdr: str, str: Any, *, file: _File = ...) -> Tuple[str, List[str]]: ...
     def xover(self, start: int, end: int, *, file: _File = ...) -> Tuple[str, List[Tuple[int, Dict[str, str]]]]: ...
     def over(
-        self, message_spec: Union[None, str, List[Any], Tuple[Any, ...]], *, file: _File = ...
+        self, message_spec: None | str | List[Any] | Tuple[Any, ...], *, file: _File = ...
     ) -> Tuple[str, List[Tuple[int, Dict[str, str]]]]: ...
     def xgtitle(self, group: str, *, file: _File = ...) -> Tuple[str, List[Tuple[str, str]]]: ...
     def xpath(self, id: Any) -> Tuple[str, str]: ...
     def date(self) -> Tuple[str, datetime.datetime]: ...
-    def post(self, data: Union[bytes, Iterable[bytes]]) -> str: ...
-    def ihave(self, message_id: Any, data: Union[bytes, Iterable[bytes]]) -> str: ...
+    def post(self, data: bytes | Iterable[bytes]) -> str: ...
+    def ihave(self, message_id: Any, data: bytes | Iterable[bytes]) -> str: ...
     def quit(self) -> str: ...
-    def login(self, user: Optional[str] = ..., password: Optional[str] = ..., usenetrc: bool = ...) -> None: ...
-    def starttls(self, context: Optional[ssl.SSLContext] = ...) -> None: ...
+    def login(self, user: str | None = ..., password: str | None = ..., usenetrc: bool = ...) -> None: ...
+    def starttls(self, context: ssl.SSLContext | None = ...) -> None: ...
 
 class NNTP(_NNTPBase):
     port: int
@@ -89,9 +87,9 @@ class NNTP(_NNTPBase):
         self,
         host: str,
         port: int = ...,
-        user: Optional[str] = ...,
-        password: Optional[str] = ...,
-        readermode: Optional[bool] = ...,
+        user: str | None = ...,
+        password: str | None = ...,
+        readermode: bool | None = ...,
         usenetrc: bool = ...,
         timeout: float = ...,
     ) -> None: ...
@@ -102,10 +100,10 @@ class NNTP_SSL(_NNTPBase):
         self,
         host: str,
         port: int = ...,
-        user: Optional[str] = ...,
-        password: Optional[str] = ...,
-        ssl_context: Optional[ssl.SSLContext] = ...,
-        readermode: Optional[bool] = ...,
+        user: str | None = ...,
+        password: str | None = ...,
+        ssl_context: ssl.SSLContext | None = ...,
+        readermode: bool | None = ...,
         usenetrc: bool = ...,
         timeout: float = ...,
     ) -> None: ...
diff --git a/stdlib/@python2/ntpath.pyi b/stdlib/@python2/ntpath.pyi
index 07bd9653efd9..514db760886f 100644
--- a/stdlib/@python2/ntpath.pyi
+++ b/stdlib/@python2/ntpath.pyi
@@ -1,7 +1,7 @@
 import os
 import sys
 from genericpath import exists as exists
-from typing import Any, AnyStr, Callable, List, Optional, Sequence, Text, Tuple, TypeVar, overload
+from typing import Any, AnyStr, Callable, List, Sequence, Text, Tuple, TypeVar, overload
 
 _T = TypeVar("_T")
 
@@ -14,7 +14,7 @@ sep: str
 if sys.platform == "win32":
     altsep: str
 else:
-    altsep: Optional[str]
+    altsep: str | None
 extsep: str
 pathsep: str
 defpath: str
@@ -68,9 +68,9 @@ def join(__p1: bytes, __p2: Text, *p: Text) -> Text: ...
 @overload
 def join(__p1: Text, *p: Text) -> Text: ...
 @overload
-def relpath(path: str, start: Optional[str] = ...) -> str: ...
+def relpath(path: str, start: str | None = ...) -> str: ...
 @overload
-def relpath(path: Text, start: Optional[Text] = ...) -> Text: ...
+def relpath(path: Text, start: Text | None = ...) -> Text: ...
 def samefile(f1: Text, f2: Text) -> bool: ...
 def sameopenfile(fp1: int, fp2: int) -> bool: ...
 def samestat(s1: os.stat_result, s2: os.stat_result) -> bool: ...
diff --git a/stdlib/@python2/numbers.pyi b/stdlib/@python2/numbers.pyi
index fa0c0a17b8a7..fb88e076d446 100644
--- a/stdlib/@python2/numbers.pyi
+++ b/stdlib/@python2/numbers.pyi
@@ -2,7 +2,7 @@
 # signatures are currently omitted.
 
 from abc import ABCMeta, abstractmethod
-from typing import Any, Optional, SupportsFloat
+from typing import Any, SupportsFloat
 
 class Number(metaclass=ABCMeta):
     @abstractmethod
@@ -89,7 +89,7 @@ class Integral(Rational):
     def __long__(self) -> long: ...
     def __index__(self) -> int: ...
     @abstractmethod
-    def __pow__(self, exponent: Any, modulus: Optional[Any] = ...) -> Any: ...
+    def __pow__(self, exponent: Any, modulus: Any | None = ...) -> Any: ...
     @abstractmethod
     def __lshift__(self, other: Any) -> Any: ...
     @abstractmethod
diff --git a/stdlib/@python2/optparse.pyi b/stdlib/@python2/optparse.pyi
index 62ae8ef8a8bf..08a926e301b3 100644
--- a/stdlib/@python2/optparse.pyi
+++ b/stdlib/@python2/optparse.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, AnyStr, Callable, Dict, Iterable, List, Mapping, Optional, Sequence, Tuple, Type, Union, overload
+from typing import IO, Any, AnyStr, Callable, Dict, Iterable, List, Mapping, Sequence, Tuple, Type, Union, overload
 
 # See https://groups.google.com/forum/#!topic/python-ideas/gA1gdj3RZ5g
 _Text = Union[str, unicode]
@@ -46,7 +46,7 @@ class HelpFormatter:
     parser: OptionParser
     short_first: Any
     width: int
-    def __init__(self, indent_increment: int, max_help_position: int, width: Optional[int], short_first: int) -> None: ...
+    def __init__(self, indent_increment: int, max_help_position: int, width: int | None, short_first: int) -> None: ...
     def dedent(self) -> None: ...
     def expand_default(self, option: Option) -> _Text: ...
     def format_description(self, description: _Text) -> _Text: ...
@@ -63,14 +63,14 @@ class HelpFormatter:
 
 class IndentedHelpFormatter(HelpFormatter):
     def __init__(
-        self, indent_increment: int = ..., max_help_position: int = ..., width: Optional[int] = ..., short_first: int = ...
+        self, indent_increment: int = ..., max_help_position: int = ..., width: int | None = ..., short_first: int = ...
     ) -> None: ...
     def format_heading(self, heading: _Text) -> _Text: ...
     def format_usage(self, usage: _Text) -> _Text: ...
 
 class TitledHelpFormatter(HelpFormatter):
     def __init__(
-        self, indent_increment: int = ..., max_help_position: int = ..., width: Optional[int] = ..., short_first: int = ...
+        self, indent_increment: int = ..., max_help_position: int = ..., width: int | None = ..., short_first: int = ...
     ) -> None: ...
     def format_heading(self, heading: _Text) -> _Text: ...
     def format_usage(self, usage: _Text) -> _Text: ...
@@ -79,7 +79,7 @@ class Option:
     ACTIONS: Tuple[_Text, ...]
     ALWAYS_TYPED_ACTIONS: Tuple[_Text, ...]
     ATTRS: List[_Text]
-    CHECK_METHODS: Optional[List[Callable[..., Any]]]
+    CHECK_METHODS: List[Callable[..., Any]] | None
     CONST_ACTIONS: Tuple[_Text, ...]
     STORE_ACTIONS: Tuple[_Text, ...]
     TYPED_ACTIONS: Tuple[_Text, ...]
@@ -88,23 +88,23 @@ class Option:
     _long_opts: List[_Text]
     _short_opts: List[_Text]
     action: _Text
-    dest: Optional[_Text]
+    dest: _Text | None
     default: Any
     nargs: int
     type: Any
-    callback: Optional[Callable[..., Any]]
-    callback_args: Optional[Tuple[Any, ...]]
-    callback_kwargs: Optional[Dict[_Text, Any]]
-    help: Optional[_Text]
-    metavar: Optional[_Text]
-    def __init__(self, *opts: Optional[_Text], **attrs: Any) -> None: ...
+    callback: Callable[..., Any] | None
+    callback_args: Tuple[Any, ...] | None
+    callback_kwargs: Dict[_Text, Any] | None
+    help: _Text | None
+    metavar: _Text | None
+    def __init__(self, *opts: _Text | None, **attrs: Any) -> None: ...
     def _check_action(self) -> None: ...
     def _check_callback(self) -> None: ...
     def _check_choice(self) -> None: ...
     def _check_const(self) -> None: ...
     def _check_dest(self) -> None: ...
     def _check_nargs(self) -> None: ...
-    def _check_opt_strings(self, opts: Iterable[Optional[_Text]]) -> List[_Text]: ...
+    def _check_opt_strings(self, opts: Iterable[_Text | None]) -> List[_Text]: ...
     def _check_type(self) -> None: ...
     def _set_attrs(self, attrs: Dict[_Text, Any]) -> None: ...
     def _set_opt_strings(self, opts: Iterable[_Text]) -> None: ...
@@ -131,14 +131,14 @@ class OptionContainer:
     @overload
     def add_option(self, opt: Option) -> Option: ...
     @overload
-    def add_option(self, *args: Optional[_Text], **kwargs: Any) -> Any: ...
+    def add_option(self, *args: _Text | None, **kwargs: Any) -> Any: ...
     def add_options(self, option_list: Iterable[Option]) -> None: ...
     def destroy(self) -> None: ...
-    def format_description(self, formatter: Optional[HelpFormatter]) -> Any: ...
-    def format_help(self, formatter: Optional[HelpFormatter]) -> _Text: ...
-    def format_option_help(self, formatter: Optional[HelpFormatter]) -> _Text: ...
+    def format_description(self, formatter: HelpFormatter | None) -> Any: ...
+    def format_help(self, formatter: HelpFormatter | None) -> _Text: ...
+    def format_option_help(self, formatter: HelpFormatter | None) -> _Text: ...
     def get_description(self) -> Any: ...
-    def get_option(self, opt_str: _Text) -> Optional[Option]: ...
+    def get_option(self, opt_str: _Text) -> Option | None: ...
     def has_option(self, opt_str: _Text) -> bool: ...
     def remove_option(self, opt_str: _Text) -> None: ...
     def set_conflict_handler(self, handler: Any) -> None: ...
@@ -148,12 +148,12 @@ class OptionGroup(OptionContainer):
     option_list: List[Option]
     parser: OptionParser
     title: _Text
-    def __init__(self, parser: OptionParser, title: _Text, description: Optional[_Text] = ...) -> None: ...
+    def __init__(self, parser: OptionParser, title: _Text, description: _Text | None = ...) -> None: ...
     def _create_option_list(self) -> None: ...
     def set_title(self, title: _Text) -> None: ...
 
 class Values:
-    def __init__(self, defaults: Optional[Mapping[str, Any]] = ...) -> None: ...
+    def __init__(self, defaults: Mapping[str, Any] | None = ...) -> None: ...
     def _update(self, dict: Mapping[_Text, Any], mode: Any) -> None: ...
     def _update_careful(self, dict: Mapping[_Text, Any]) -> None: ...
     def _update_loose(self, dict: Mapping[_Text, Any]) -> None: ...
@@ -165,30 +165,30 @@ class Values:
 
 class OptionParser(OptionContainer):
     allow_interspersed_args: bool
-    epilog: Optional[_Text]
+    epilog: _Text | None
     formatter: HelpFormatter
-    largs: Optional[List[_Text]]
+    largs: List[_Text] | None
     option_groups: List[OptionGroup]
     option_list: List[Option]
     process_default_values: Any
-    prog: Optional[_Text]
-    rargs: Optional[List[Any]]
+    prog: _Text | None
+    rargs: List[Any] | None
     standard_option_list: List[Option]
-    usage: Optional[_Text]
-    values: Optional[Values]
+    usage: _Text | None
+    values: Values | None
     version: _Text
     def __init__(
         self,
-        usage: Optional[_Text] = ...,
-        option_list: Optional[Iterable[Option]] = ...,
+        usage: _Text | None = ...,
+        option_list: Iterable[Option] | None = ...,
         option_class: Type[Option] = ...,
-        version: Optional[_Text] = ...,
+        version: _Text | None = ...,
         conflict_handler: _Text = ...,
-        description: Optional[_Text] = ...,
-        formatter: Optional[HelpFormatter] = ...,
+        description: _Text | None = ...,
+        formatter: HelpFormatter | None = ...,
         add_help_option: bool = ...,
-        prog: Optional[_Text] = ...,
-        epilog: Optional[_Text] = ...,
+        prog: _Text | None = ...,
+        epilog: _Text | None = ...,
     ) -> None: ...
     def _add_help_option(self) -> None: ...
     def _add_version_option(self) -> None: ...
@@ -209,22 +209,20 @@ class OptionParser(OptionContainer):
     def disable_interspersed_args(self) -> None: ...
     def enable_interspersed_args(self) -> None: ...
     def error(self, msg: _Text) -> None: ...
-    def exit(self, status: int = ..., msg: Optional[str] = ...) -> None: ...
-    def expand_prog_name(self, s: Optional[_Text]) -> Any: ...
+    def exit(self, status: int = ..., msg: str | None = ...) -> None: ...
+    def expand_prog_name(self, s: _Text | None) -> Any: ...
     def format_epilog(self, formatter: HelpFormatter) -> Any: ...
-    def format_help(self, formatter: Optional[HelpFormatter] = ...) -> _Text: ...
-    def format_option_help(self, formatter: Optional[HelpFormatter] = ...) -> _Text: ...
+    def format_help(self, formatter: HelpFormatter | None = ...) -> _Text: ...
+    def format_option_help(self, formatter: HelpFormatter | None = ...) -> _Text: ...
     def get_default_values(self) -> Values: ...
     def get_option_group(self, opt_str: _Text) -> Any: ...
     def get_prog_name(self) -> _Text: ...
     def get_usage(self) -> _Text: ...
     def get_version(self) -> _Text: ...
-    def parse_args(
-        self, args: Optional[Sequence[AnyStr]] = ..., values: Optional[Values] = ...
-    ) -> Tuple[Values, List[AnyStr]]: ...
-    def print_usage(self, file: Optional[IO[str]] = ...) -> None: ...
-    def print_help(self, file: Optional[IO[str]] = ...) -> None: ...
-    def print_version(self, file: Optional[IO[str]] = ...) -> None: ...
+    def parse_args(self, args: Sequence[AnyStr] | None = ..., values: Values | None = ...) -> Tuple[Values, List[AnyStr]]: ...
+    def print_usage(self, file: IO[str] | None = ...) -> None: ...
+    def print_help(self, file: IO[str] | None = ...) -> None: ...
+    def print_version(self, file: IO[str] | None = ...) -> None: ...
     def set_default(self, dest: Any, value: Any) -> None: ...
     def set_defaults(self, **kwargs: Any) -> None: ...
     def set_process_default_values(self, process: Any) -> None: ...
diff --git a/stdlib/@python2/os/__init__.pyi b/stdlib/@python2/os/__init__.pyi
index 3b4f9698dd14..1955c07020de 100644
--- a/stdlib/@python2/os/__init__.pyi
+++ b/stdlib/@python2/os/__init__.pyi
@@ -15,7 +15,6 @@ from typing import (
     MutableMapping,
     NamedTuple,
     NoReturn,
-    Optional,
     Sequence,
     Text,
     Tuple,
@@ -77,7 +76,7 @@ sep: str
 if sys.platform == "win32":
     altsep: str
 else:
-    altsep: Optional[str]
+    altsep: str | None
 extsep: str
 pathsep: str
 defpath: str
@@ -185,11 +184,11 @@ if sys.platform != "win32":
     def uname() -> Tuple[str, str, str, str, str]: ...
 
 @overload
-def getenv(key: Text) -> Optional[str]: ...
+def getenv(key: Text) -> str | None: ...
 @overload
-def getenv(key: Text, default: _T) -> Union[str, _T]: ...
-def putenv(key: Union[bytes, Text], value: Union[bytes, Text]) -> None: ...
-def unsetenv(key: Union[bytes, Text]) -> None: ...
+def getenv(key: Text, default: _T) -> str | _T: ...
+def putenv(key: bytes | Text, value: bytes | Text) -> None: ...
+def unsetenv(key: bytes | Text) -> None: ...
 def fdopen(fd: int, *args, **kwargs) -> IO[Any]: ...
 def close(fd: int) -> None: ...
 def closerange(fd_low: int, fd_high: int) -> None: ...
@@ -201,7 +200,7 @@ def lseek(fd: int, pos: int, how: int) -> int: ...
 def open(file: Text, flags: int, mode: int = ...) -> int: ...
 def pipe() -> Tuple[int, int]: ...
 def read(fd: int, n: int) -> bytes: ...
-def write(fd: int, string: Union[bytes, buffer]) -> int: ...
+def write(fd: int, string: bytes | buffer) -> int: ...
 def access(path: Text, mode: int) -> bool: ...
 def chdir(path: Text) -> None: ...
 def fchdir(fd: FileDescriptorLike) -> None: ...
@@ -231,7 +230,7 @@ def symlink(source: Text, link_name: Text) -> None: ...
 def unlink(path: Text) -> None: ...
 
 # TODO: add ns, dir_fd, follow_symlinks argument
-def utime(path: Text, times: Optional[Tuple[float, float]]) -> None: ...
+def utime(path: Text, times: Tuple[float, float] | None) -> None: ...
 
 if sys.platform != "win32":
     # Unix only
@@ -239,7 +238,7 @@ if sys.platform != "win32":
     def fchown(fd: int, uid: int, gid: int) -> None: ...
     if sys.platform != "darwin":
         def fdatasync(fd: FileDescriptorLike) -> None: ...  # Unix only, not Mac
-    def fpathconf(fd: int, name: Union[str, int]) -> int: ...
+    def fpathconf(fd: int, name: str | int) -> int: ...
     def fstatvfs(fd: int) -> _StatVFS: ...
     def ftruncate(fd: int, length: int) -> None: ...
     def isatty(fd: int) -> bool: ...
@@ -254,21 +253,21 @@ if sys.platform != "win32":
     def lchmod(path: Text, mode: int) -> None: ...
     def lchown(path: Text, uid: int, gid: int) -> None: ...
     def mkfifo(path: Text, mode: int = ...) -> None: ...
-    def pathconf(path: Text, name: Union[str, int]) -> int: ...
+    def pathconf(path: Text, name: str | int) -> int: ...
     def statvfs(path: Text) -> _StatVFS: ...
 
 def walk(
-    top: AnyStr, topdown: bool = ..., onerror: Optional[Callable[[OSError], Any]] = ..., followlinks: bool = ...
+    top: AnyStr, topdown: bool = ..., onerror: Callable[[OSError], Any] | None = ..., followlinks: bool = ...
 ) -> Iterator[Tuple[AnyStr, List[AnyStr], List[AnyStr]]]: ...
 def abort() -> NoReturn: ...
 
 # These are defined as execl(file, *args) but the first *arg is mandatory.
-def execl(file: Text, __arg0: Union[bytes, Text], *args: Union[bytes, Text]) -> NoReturn: ...
-def execlp(file: Text, __arg0: Union[bytes, Text], *args: Union[bytes, Text]) -> NoReturn: ...
+def execl(file: Text, __arg0: bytes | Text, *args: bytes | Text) -> NoReturn: ...
+def execlp(file: Text, __arg0: bytes | Text, *args: bytes | Text) -> NoReturn: ...
 
 # These are: execle(file, *args, env) but env is pulled from the last element of the args.
-def execle(file: Text, __arg0: Union[bytes, Text], *args: Any) -> NoReturn: ...
-def execlpe(file: Text, __arg0: Union[bytes, Text], *args: Any) -> NoReturn: ...
+def execle(file: Text, __arg0: bytes | Text, *args: Any) -> NoReturn: ...
+def execlpe(file: Text, __arg0: bytes | Text, *args: Any) -> NoReturn: ...
 
 # The docs say `args: tuple or list of strings`
 # The implementation enforces tuple or list so we can't use Sequence.
@@ -293,24 +292,24 @@ def popen(command: str, *args, **kwargs) -> IO[Any]: ...
 def popen2(cmd: str, *args, **kwargs) -> Tuple[IO[Any], IO[Any]]: ...
 def popen3(cmd: str, *args, **kwargs) -> Tuple[IO[Any], IO[Any], IO[Any]]: ...
 def popen4(cmd: str, *args, **kwargs) -> Tuple[IO[Any], IO[Any]]: ...
-def spawnl(mode: int, path: Text, arg0: Union[bytes, Text], *args: Union[bytes, Text]) -> int: ...
-def spawnle(mode: int, path: Text, arg0: Union[bytes, Text], *args: Any) -> int: ...  # Imprecise sig
-def spawnv(mode: int, path: Text, args: List[Union[bytes, Text]]) -> int: ...
-def spawnve(mode: int, path: Text, args: List[Union[bytes, Text]], env: Mapping[str, str]) -> int: ...
+def spawnl(mode: int, path: Text, arg0: bytes | Text, *args: bytes | Text) -> int: ...
+def spawnle(mode: int, path: Text, arg0: bytes | Text, *args: Any) -> int: ...  # Imprecise sig
+def spawnv(mode: int, path: Text, args: List[bytes | Text]) -> int: ...
+def spawnve(mode: int, path: Text, args: List[bytes | Text], env: Mapping[str, str]) -> int: ...
 def system(command: Text) -> int: ...
 def times() -> Tuple[float, float, float, float, float]: ...
 def waitpid(pid: int, options: int) -> Tuple[int, int]: ...
 def urandom(n: int) -> bytes: ...
 
 if sys.platform == "win32":
-    def startfile(path: Text, operation: Optional[str] = ...) -> None: ...
+    def startfile(path: Text, operation: str | None = ...) -> None: ...
 
 else:
     # Unix only
-    def spawnlp(mode: int, file: Text, arg0: Union[bytes, Text], *args: Union[bytes, Text]) -> int: ...
-    def spawnlpe(mode: int, file: Text, arg0: Union[bytes, Text], *args: Any) -> int: ...  # Imprecise signature
-    def spawnvp(mode: int, file: Text, args: List[Union[bytes, Text]]) -> int: ...
-    def spawnvpe(mode: int, file: Text, args: List[Union[bytes, Text]], env: Mapping[str, str]) -> int: ...
+    def spawnlp(mode: int, file: Text, arg0: bytes | Text, *args: bytes | Text) -> int: ...
+    def spawnlpe(mode: int, file: Text, arg0: bytes | Text, *args: Any) -> int: ...  # Imprecise signature
+    def spawnvp(mode: int, file: Text, args: List[bytes | Text]) -> int: ...
+    def spawnvpe(mode: int, file: Text, args: List[bytes | Text], env: Mapping[str, str]) -> int: ...
     def wait() -> Tuple[int, int]: ...
     def wait3(options: int) -> Tuple[int, int, Any]: ...
     def wait4(pid: int, options: int) -> Tuple[int, int, Any]: ...
@@ -322,9 +321,9 @@ else:
     def WEXITSTATUS(status: int) -> int: ...
     def WSTOPSIG(status: int) -> int: ...
     def WTERMSIG(status: int) -> int: ...
-    def confstr(name: Union[str, int]) -> Optional[str]: ...
+    def confstr(name: str | int) -> str | None: ...
     def getloadavg() -> Tuple[float, float, float]: ...
-    def sysconf(name: Union[str, int]) -> int: ...
+    def sysconf(name: str | int) -> int: ...
 
 def tmpfile() -> IO[Any]: ...
 def tmpnam() -> str: ...
diff --git a/stdlib/@python2/os/path.pyi b/stdlib/@python2/os/path.pyi
index 124385f1301d..2ce2f592f0e2 100644
--- a/stdlib/@python2/os/path.pyi
+++ b/stdlib/@python2/os/path.pyi
@@ -1,6 +1,6 @@
 import os
 import sys
-from typing import Any, AnyStr, Callable, List, Optional, Sequence, Text, Tuple, TypeVar, overload
+from typing import Any, AnyStr, Callable, List, Sequence, Text, Tuple, TypeVar, overload
 
 _T = TypeVar("_T")
 
@@ -13,7 +13,7 @@ sep: str
 if sys.platform == "win32":
     altsep: str
 else:
-    altsep: Optional[str]
+    altsep: str | None
 extsep: str
 pathsep: str
 defpath: str
@@ -68,9 +68,9 @@ def join(__p1: bytes, __p2: Text, *p: Text) -> Text: ...
 @overload
 def join(__p1: Text, *p: Text) -> Text: ...
 @overload
-def relpath(path: str, start: Optional[str] = ...) -> str: ...
+def relpath(path: str, start: str | None = ...) -> str: ...
 @overload
-def relpath(path: Text, start: Optional[Text] = ...) -> Text: ...
+def relpath(path: Text, start: Text | None = ...) -> Text: ...
 def samefile(f1: Text, f2: Text) -> bool: ...
 def sameopenfile(fp1: int, fp2: int) -> bool: ...
 def samestat(s1: os.stat_result, s2: os.stat_result) -> bool: ...
diff --git a/stdlib/@python2/os2emxpath.pyi b/stdlib/@python2/os2emxpath.pyi
index 07bd9653efd9..514db760886f 100644
--- a/stdlib/@python2/os2emxpath.pyi
+++ b/stdlib/@python2/os2emxpath.pyi
@@ -1,7 +1,7 @@
 import os
 import sys
 from genericpath import exists as exists
-from typing import Any, AnyStr, Callable, List, Optional, Sequence, Text, Tuple, TypeVar, overload
+from typing import Any, AnyStr, Callable, List, Sequence, Text, Tuple, TypeVar, overload
 
 _T = TypeVar("_T")
 
@@ -14,7 +14,7 @@ sep: str
 if sys.platform == "win32":
     altsep: str
 else:
-    altsep: Optional[str]
+    altsep: str | None
 extsep: str
 pathsep: str
 defpath: str
@@ -68,9 +68,9 @@ def join(__p1: bytes, __p2: Text, *p: Text) -> Text: ...
 @overload
 def join(__p1: Text, *p: Text) -> Text: ...
 @overload
-def relpath(path: str, start: Optional[str] = ...) -> str: ...
+def relpath(path: str, start: str | None = ...) -> str: ...
 @overload
-def relpath(path: Text, start: Optional[Text] = ...) -> Text: ...
+def relpath(path: Text, start: Text | None = ...) -> Text: ...
 def samefile(f1: Text, f2: Text) -> bool: ...
 def sameopenfile(fp1: int, fp2: int) -> bool: ...
 def samestat(s1: os.stat_result, s2: os.stat_result) -> bool: ...
diff --git a/stdlib/@python2/pdb.pyi b/stdlib/@python2/pdb.pyi
index ba04e4d28fab..6d3a6d5c5903 100644
--- a/stdlib/@python2/pdb.pyi
+++ b/stdlib/@python2/pdb.pyi
@@ -1,7 +1,7 @@
 from bdb import Bdb
 from cmd import Cmd
 from types import FrameType, TracebackType
-from typing import IO, Any, Callable, ClassVar, Dict, Iterable, List, Mapping, Optional, Tuple, TypeVar, Union
+from typing import IO, Any, Callable, ClassVar, Dict, Iterable, List, Mapping, Tuple, TypeVar
 
 _T = TypeVar("_T")
 
@@ -9,12 +9,12 @@ line_prefix: str  # undocumented
 
 class Restart(Exception): ...
 
-def run(statement: str, globals: Optional[Dict[str, Any]] = ..., locals: Optional[Mapping[str, Any]] = ...) -> None: ...
-def runeval(expression: str, globals: Optional[Dict[str, Any]] = ..., locals: Optional[Mapping[str, Any]] = ...) -> Any: ...
+def run(statement: str, globals: Dict[str, Any] | None = ..., locals: Mapping[str, Any] | None = ...) -> None: ...
+def runeval(expression: str, globals: Dict[str, Any] | None = ..., locals: Mapping[str, Any] | None = ...) -> Any: ...
 def runctx(statement: str, globals: Dict[str, Any], locals: Mapping[str, Any]) -> None: ...
-def runcall(func: Callable[..., _T], *args: Any, **kwds: Any) -> Optional[_T]: ...
+def runcall(func: Callable[..., _T], *args: Any, **kwds: Any) -> _T | None: ...
 def set_trace() -> None: ...
-def post_mortem(t: Optional[TracebackType] = ...) -> None: ...
+def post_mortem(t: TracebackType | None = ...) -> None: ...
 def pm() -> None: ...
 
 class Pdb(Bdb, Cmd):
@@ -30,64 +30,60 @@ class Pdb(Bdb, Cmd):
     commands_doprompt: Dict[int, bool]
     commands_silent: Dict[int, bool]
     commands_defining: bool
-    commands_bnum: Optional[int]
-    lineno: Optional[int]
+    commands_bnum: int | None
+    lineno: int | None
     stack: List[Tuple[FrameType, int]]
     curindex: int
-    curframe: Optional[FrameType]
+    curframe: FrameType | None
     curframe_locals: Mapping[str, Any]
     def __init__(
-        self,
-        completekey: str = ...,
-        stdin: Optional[IO[str]] = ...,
-        stdout: Optional[IO[str]] = ...,
-        skip: Optional[Iterable[str]] = ...,
+        self, completekey: str = ..., stdin: IO[str] | None = ..., stdout: IO[str] | None = ..., skip: Iterable[str] | None = ...
     ) -> None: ...
     def forget(self) -> None: ...
-    def setup(self, f: Optional[FrameType], tb: Optional[TracebackType]) -> None: ...
+    def setup(self, f: FrameType | None, tb: TracebackType | None) -> None: ...
     def execRcLines(self) -> None: ...
     def bp_commands(self, frame: FrameType) -> bool: ...
-    def interaction(self, frame: Optional[FrameType], traceback: Optional[TracebackType]) -> None: ...
+    def interaction(self, frame: FrameType | None, traceback: TracebackType | None) -> None: ...
     def displayhook(self, obj: object) -> None: ...
     def handle_command_def(self, line: str) -> bool: ...
     def defaultFile(self) -> str: ...
-    def lineinfo(self, identifier: str) -> Union[Tuple[None, None, None], Tuple[str, str, int]]: ...
+    def lineinfo(self, identifier: str) -> Tuple[None, None, None] | Tuple[str, str, int]: ...
     def checkline(self, filename: str, lineno: int) -> int: ...
     def _getval(self, arg: str) -> object: ...
     def print_stack_trace(self) -> None: ...
     def print_stack_entry(self, frame_lineno: Tuple[FrameType, int], prompt_prefix: str = ...) -> None: ...
-    def lookupmodule(self, filename: str) -> Optional[str]: ...
+    def lookupmodule(self, filename: str) -> str | None: ...
     def _runscript(self, filename: str) -> None: ...
-    def do_commands(self, arg: str) -> Optional[bool]: ...
-    def do_break(self, arg: str, temporary: bool = ...) -> Optional[bool]: ...
-    def do_tbreak(self, arg: str) -> Optional[bool]: ...
-    def do_enable(self, arg: str) -> Optional[bool]: ...
-    def do_disable(self, arg: str) -> Optional[bool]: ...
-    def do_condition(self, arg: str) -> Optional[bool]: ...
-    def do_ignore(self, arg: str) -> Optional[bool]: ...
-    def do_clear(self, arg: str) -> Optional[bool]: ...
-    def do_where(self, arg: str) -> Optional[bool]: ...
-    def do_up(self, arg: str) -> Optional[bool]: ...
-    def do_down(self, arg: str) -> Optional[bool]: ...
-    def do_until(self, arg: str) -> Optional[bool]: ...
-    def do_step(self, arg: str) -> Optional[bool]: ...
-    def do_next(self, arg: str) -> Optional[bool]: ...
-    def do_run(self, arg: str) -> Optional[bool]: ...
-    def do_return(self, arg: str) -> Optional[bool]: ...
-    def do_continue(self, arg: str) -> Optional[bool]: ...
-    def do_jump(self, arg: str) -> Optional[bool]: ...
-    def do_debug(self, arg: str) -> Optional[bool]: ...
-    def do_quit(self, arg: str) -> Optional[bool]: ...
-    def do_EOF(self, arg: str) -> Optional[bool]: ...
-    def do_args(self, arg: str) -> Optional[bool]: ...
-    def do_retval(self, arg: str) -> Optional[bool]: ...
-    def do_p(self, arg: str) -> Optional[bool]: ...
-    def do_pp(self, arg: str) -> Optional[bool]: ...
-    def do_list(self, arg: str) -> Optional[bool]: ...
-    def do_whatis(self, arg: str) -> Optional[bool]: ...
-    def do_alias(self, arg: str) -> Optional[bool]: ...
-    def do_unalias(self, arg: str) -> Optional[bool]: ...
-    def do_help(self, arg: str) -> Optional[bool]: ...
+    def do_commands(self, arg: str) -> bool | None: ...
+    def do_break(self, arg: str, temporary: bool = ...) -> bool | None: ...
+    def do_tbreak(self, arg: str) -> bool | None: ...
+    def do_enable(self, arg: str) -> bool | None: ...
+    def do_disable(self, arg: str) -> bool | None: ...
+    def do_condition(self, arg: str) -> bool | None: ...
+    def do_ignore(self, arg: str) -> bool | None: ...
+    def do_clear(self, arg: str) -> bool | None: ...
+    def do_where(self, arg: str) -> bool | None: ...
+    def do_up(self, arg: str) -> bool | None: ...
+    def do_down(self, arg: str) -> bool | None: ...
+    def do_until(self, arg: str) -> bool | None: ...
+    def do_step(self, arg: str) -> bool | None: ...
+    def do_next(self, arg: str) -> bool | None: ...
+    def do_run(self, arg: str) -> bool | None: ...
+    def do_return(self, arg: str) -> bool | None: ...
+    def do_continue(self, arg: str) -> bool | None: ...
+    def do_jump(self, arg: str) -> bool | None: ...
+    def do_debug(self, arg: str) -> bool | None: ...
+    def do_quit(self, arg: str) -> bool | None: ...
+    def do_EOF(self, arg: str) -> bool | None: ...
+    def do_args(self, arg: str) -> bool | None: ...
+    def do_retval(self, arg: str) -> bool | None: ...
+    def do_p(self, arg: str) -> bool | None: ...
+    def do_pp(self, arg: str) -> bool | None: ...
+    def do_list(self, arg: str) -> bool | None: ...
+    def do_whatis(self, arg: str) -> bool | None: ...
+    def do_alias(self, arg: str) -> bool | None: ...
+    def do_unalias(self, arg: str) -> bool | None: ...
+    def do_help(self, arg: str) -> bool | None: ...
     do_b = do_break
     do_cl = do_clear
     do_w = do_where
@@ -161,7 +157,7 @@ class Pdb(Bdb, Cmd):
 
 # undocumented
 
-def find_function(funcname: str, filename: str) -> Optional[Tuple[str, str, int]]: ...
+def find_function(funcname: str, filename: str) -> Tuple[str, str, int] | None: ...
 def main() -> None: ...
 def help() -> None: ...
 
diff --git a/stdlib/@python2/pickle.pyi b/stdlib/@python2/pickle.pyi
index 8272caeeed23..07e32e64b449 100644
--- a/stdlib/@python2/pickle.pyi
+++ b/stdlib/@python2/pickle.pyi
@@ -3,8 +3,8 @@ from typing import IO, Any, Callable, Iterator, Optional, Tuple, Type, Union
 HIGHEST_PROTOCOL: int
 bytes_types: Tuple[Type[Any], ...]  # undocumented
 
-def dump(obj: Any, file: IO[bytes], protocol: Optional[int] = ...) -> None: ...
-def dumps(obj: Any, protocol: Optional[int] = ...) -> bytes: ...
+def dump(obj: Any, file: IO[bytes], protocol: int | None = ...) -> None: ...
+def dumps(obj: Any, protocol: int | None = ...) -> bytes: ...
 def load(file: IO[bytes]) -> Any: ...
 def loads(string: bytes) -> Any: ...
 
@@ -22,7 +22,7 @@ _reducedtype = Union[
 
 class Pickler:
     fast: bool
-    def __init__(self, file: IO[bytes], protocol: Optional[int] = ...) -> None: ...
+    def __init__(self, file: IO[bytes], protocol: int | None = ...) -> None: ...
     def dump(self, __obj: Any) -> None: ...
     def clear_memo(self) -> None: ...
     def persistent_id(self, obj: Any) -> Any: ...
diff --git a/stdlib/@python2/pickletools.pyi b/stdlib/@python2/pickletools.pyi
index 154aaf174f5d..14ec0fdff03a 100644
--- a/stdlib/@python2/pickletools.pyi
+++ b/stdlib/@python2/pickletools.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, Callable, Iterator, List, MutableMapping, Optional, Text, Tuple, Type, Union
+from typing import IO, Any, Callable, Iterator, List, MutableMapping, Text, Tuple, Type
 
 _Reader = Callable[[IO[bytes]], Any]
 
@@ -25,7 +25,7 @@ def read_int4(f: IO[bytes]) -> int: ...
 
 int4: ArgumentDescriptor
 
-def read_stringnl(f: IO[bytes], decode: bool = ..., stripquotes: bool = ...) -> Union[bytes, Text]: ...
+def read_stringnl(f: IO[bytes], decode: bool = ..., stripquotes: bool = ...) -> bytes | Text: ...
 
 stringnl: ArgumentDescriptor
 
@@ -77,9 +77,9 @@ long4: ArgumentDescriptor
 
 class StackObject(object):
     name: str
-    obtype: Union[Type[Any], Tuple[Type[Any], ...]]
+    obtype: Type[Any] | Tuple[Type[Any], ...]
     doc: str
-    def __init__(self, name: str, obtype: Union[Type[Any], Tuple[Type[Any], ...]], doc: str) -> None: ...
+    def __init__(self, name: str, obtype: Type[Any] | Tuple[Type[Any], ...], doc: str) -> None: ...
 
 pyint: StackObject
 pylong: StackObject
@@ -99,7 +99,7 @@ stackslice: StackObject
 class OpcodeInfo(object):
     name: str
     code: str
-    arg: Optional[ArgumentDescriptor]
+    arg: ArgumentDescriptor | None
     stack_before: List[StackObject]
     stack_after: List[StackObject]
     proto: int
@@ -108,7 +108,7 @@ class OpcodeInfo(object):
         self,
         name: str,
         code: str,
-        arg: Optional[ArgumentDescriptor],
+        arg: ArgumentDescriptor | None,
         stack_before: List[StackObject],
         stack_after: List[StackObject],
         proto: int,
@@ -117,11 +117,8 @@ class OpcodeInfo(object):
 
 opcodes: List[OpcodeInfo]
 
-def genops(pickle: Union[bytes, IO[bytes]]) -> Iterator[Tuple[OpcodeInfo, Optional[Any], Optional[int]]]: ...
-def optimize(p: Union[bytes, IO[bytes]]) -> bytes: ...
+def genops(pickle: bytes | IO[bytes]) -> Iterator[Tuple[OpcodeInfo, Any | None, int | None]]: ...
+def optimize(p: bytes | IO[bytes]) -> bytes: ...
 def dis(
-    pickle: Union[bytes, IO[bytes]],
-    out: Optional[IO[str]] = ...,
-    memo: Optional[MutableMapping[int, Any]] = ...,
-    indentlevel: int = ...,
+    pickle: bytes | IO[bytes], out: IO[str] | None = ..., memo: MutableMapping[int, Any] | None = ..., indentlevel: int = ...
 ) -> None: ...
diff --git a/stdlib/@python2/pkgutil.pyi b/stdlib/@python2/pkgutil.pyi
index 5fefef39bd6b..fd42af916cfe 100644
--- a/stdlib/@python2/pkgutil.pyi
+++ b/stdlib/@python2/pkgutil.pyi
@@ -1,5 +1,5 @@
 from _typeshed import SupportsRead
-from typing import IO, Any, Callable, Iterable, Iterator, List, Optional, Tuple, Union
+from typing import IO, Any, Callable, Iterable, Iterator, List, Tuple, Union
 
 Loader = Any
 MetaPathFinder = Any
@@ -10,18 +10,18 @@ _ModuleInfoLike = Tuple[Union[MetaPathFinder, PathEntryFinder], str, bool]
 def extend_path(path: List[str], name: str) -> List[str]: ...
 
 class ImpImporter:
-    def __init__(self, path: Optional[str] = ...) -> None: ...
+    def __init__(self, path: str | None = ...) -> None: ...
 
 class ImpLoader:
     def __init__(self, fullname: str, file: IO[str], filename: str, etc: Tuple[str, str, int]) -> None: ...
 
-def find_loader(fullname: str) -> Optional[Loader]: ...
-def get_importer(path_item: str) -> Optional[PathEntryFinder]: ...
+def find_loader(fullname: str) -> Loader | None: ...
+def get_importer(path_item: str) -> PathEntryFinder | None: ...
 def get_loader(module_or_name: str) -> Loader: ...
-def iter_importers(fullname: str = ...) -> Iterator[Union[MetaPathFinder, PathEntryFinder]]: ...
-def iter_modules(path: Optional[Iterable[str]] = ..., prefix: str = ...) -> Iterator[_ModuleInfoLike]: ...
+def iter_importers(fullname: str = ...) -> Iterator[MetaPathFinder | PathEntryFinder]: ...
+def iter_modules(path: Iterable[str] | None = ..., prefix: str = ...) -> Iterator[_ModuleInfoLike]: ...
 def read_code(stream: SupportsRead[bytes]) -> Any: ...  # undocumented
 def walk_packages(
-    path: Optional[Iterable[str]] = ..., prefix: str = ..., onerror: Optional[Callable[[str], None]] = ...
+    path: Iterable[str] | None = ..., prefix: str = ..., onerror: Callable[[str], None] | None = ...
 ) -> Iterator[_ModuleInfoLike]: ...
-def get_data(package: str, resource: str) -> Optional[bytes]: ...
+def get_data(package: str, resource: str) -> bytes | None: ...
diff --git a/stdlib/@python2/platform.pyi b/stdlib/@python2/platform.pyi
index 44bbe4d62aa9..b984a2b2d3d5 100644
--- a/stdlib/@python2/platform.pyi
+++ b/stdlib/@python2/platform.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Optional, Tuple
+from typing import Any, Tuple
 
 __copyright__: Any
 DEV_NULL: Any
@@ -12,13 +12,13 @@ class _popen:
     pipe: Any
     bufsize: Any
     mode: Any
-    def __init__(self, cmd, mode=..., bufsize: Optional[Any] = ...): ...
+    def __init__(self, cmd, mode=..., bufsize: Any | None = ...): ...
     def read(self): ...
     def readlines(self): ...
     def close(self, remove=..., error=...): ...
     __del__: Any
 
-def popen(cmd, mode=..., bufsize: Optional[Any] = ...): ...
+def popen(cmd, mode=..., bufsize: Any | None = ...): ...
 def win32_ver(release: str = ..., version: str = ..., csd: str = ..., ptype: str = ...) -> Tuple[str, str, str, str]: ...
 def mac_ver(
     release: str = ..., versioninfo: Tuple[str, str, str] = ..., machine: str = ...
diff --git a/stdlib/@python2/plistlib.pyi b/stdlib/@python2/plistlib.pyi
index 23115812ad69..d815e3c35404 100644
--- a/stdlib/@python2/plistlib.pyi
+++ b/stdlib/@python2/plistlib.pyi
@@ -2,8 +2,8 @@ from typing import IO, Any, Dict as DictT, Mapping, Text, Union
 
 _Path = Union[str, Text]
 
-def readPlist(pathOrFile: Union[_Path, IO[bytes]]) -> Any: ...
-def writePlist(value: Mapping[str, Any], pathOrFile: Union[_Path, IO[bytes]]) -> None: ...
+def readPlist(pathOrFile: _Path | IO[bytes]) -> Any: ...
+def writePlist(value: Mapping[str, Any], pathOrFile: _Path | IO[bytes]) -> None: ...
 def readPlistFromBytes(data: bytes) -> Any: ...
 def writePlistToBytes(value: Mapping[str, Any]) -> bytes: ...
 def readPlistFromResource(path: _Path, restype: str = ..., resid: int = ...) -> Any: ...
diff --git a/stdlib/@python2/popen2.pyi b/stdlib/@python2/popen2.pyi
index b37a71085bf4..0efee4e6d271 100644
--- a/stdlib/@python2/popen2.pyi
+++ b/stdlib/@python2/popen2.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Iterable, Optional, TextIO, Tuple, TypeVar, Union
+from typing import Any, Iterable, TextIO, Tuple, TypeVar
 
 _T = TypeVar("_T")
 
@@ -8,10 +8,10 @@ class Popen3:
     pid: int
     tochild: TextIO
     fromchild: TextIO
-    childerr: Optional[TextIO]
+    childerr: TextIO | None
     def __init__(self, cmd: Iterable[Any] = ..., capturestderr: bool = ..., bufsize: int = ...) -> None: ...
     def __del__(self) -> None: ...
-    def poll(self, _deadstate: _T = ...) -> Union[int, _T]: ...
+    def poll(self, _deadstate: _T = ...) -> int | _T: ...
     def wait(self) -> int: ...
 
 class Popen4(Popen3):
diff --git a/stdlib/@python2/poplib.pyi b/stdlib/@python2/poplib.pyi
index 603093d419a2..7a71f9850dfe 100644
--- a/stdlib/@python2/poplib.pyi
+++ b/stdlib/@python2/poplib.pyi
@@ -1,5 +1,5 @@
 import socket
-from typing import Any, BinaryIO, List, Optional, Pattern, Text, Tuple, overload
+from typing import Any, BinaryIO, List, Pattern, Text, Tuple, overload
 
 _LongResp = Tuple[bytes, List[bytes], int]
 
@@ -23,7 +23,7 @@ class POP3:
     def user(self, user: Text) -> bytes: ...
     def pass_(self, pswd: Text) -> bytes: ...
     def stat(self) -> Tuple[int, int]: ...
-    def list(self, which: Optional[Any] = ...) -> _LongResp: ...
+    def list(self, which: Any | None = ...) -> _LongResp: ...
     def retr(self, which: Any) -> _LongResp: ...
     def dele(self, which: Any) -> bytes: ...
     def noop(self) -> bytes: ...
@@ -41,5 +41,5 @@ class POP3:
 
 class POP3_SSL(POP3):
     def __init__(
-        self, host: Text, port: int = ..., keyfile: Optional[Text] = ..., certfile: Optional[Text] = ..., timeout: float = ...
+        self, host: Text, port: int = ..., keyfile: Text | None = ..., certfile: Text | None = ..., timeout: float = ...
     ) -> None: ...
diff --git a/stdlib/@python2/posix.pyi b/stdlib/@python2/posix.pyi
index ae79286ec50d..c39ce325289b 100644
--- a/stdlib/@python2/posix.pyi
+++ b/stdlib/@python2/posix.pyi
@@ -1,5 +1,5 @@
 from _typeshed import FileDescriptorLike
-from typing import IO, AnyStr, Dict, List, Mapping, NamedTuple, Optional, Sequence, Tuple, TypeVar, Union
+from typing import IO, AnyStr, Dict, List, Mapping, NamedTuple, Sequence, Tuple, TypeVar
 
 error = OSError
 
@@ -100,7 +100,7 @@ def chown(path: unicode, uid: int, gid: int) -> None: ...
 def chroot(path: unicode) -> None: ...
 def close(fd: int) -> None: ...
 def closerange(fd_low: int, fd_high: int) -> None: ...
-def confstr(name: Union[str, int]) -> str: ...
+def confstr(name: str | int) -> str: ...
 def ctermid() -> str: ...
 def dup(fd: int) -> int: ...
 def dup2(fd: int, fd2: int) -> None: ...
@@ -178,7 +178,7 @@ def statvfs(path: unicode) -> statvfs_result: ...
 def stat_float_times(fd: int) -> None: ...
 def strerror(code: int) -> str: ...
 def symlink(source: unicode, link_name: unicode) -> None: ...
-def sysconf(name: Union[str, int]) -> int: ...
+def sysconf(name: str | int) -> int: ...
 def system(command: unicode) -> int: ...
 def tcgetpgrp(fd: int) -> int: ...
 def tcsetpgrp(fd: int, pg: int) -> None: ...
@@ -190,7 +190,7 @@ def uname() -> Tuple[str, str, str, str, str]: ...
 def unlink(path: unicode) -> None: ...
 def unsetenv(varname: str) -> None: ...
 def urandom(n: int) -> str: ...
-def utime(path: unicode, times: Optional[Tuple[int, int]]) -> None: ...
+def utime(path: unicode, times: Tuple[int, int] | None) -> None: ...
 def wait() -> int: ...
 
 _r = Tuple[float, float, int, int, int, int, int, int, int, int, int, int, int, int, int, int]
diff --git a/stdlib/@python2/posixpath.pyi b/stdlib/@python2/posixpath.pyi
index 07bd9653efd9..514db760886f 100644
--- a/stdlib/@python2/posixpath.pyi
+++ b/stdlib/@python2/posixpath.pyi
@@ -1,7 +1,7 @@
 import os
 import sys
 from genericpath import exists as exists
-from typing import Any, AnyStr, Callable, List, Optional, Sequence, Text, Tuple, TypeVar, overload
+from typing import Any, AnyStr, Callable, List, Sequence, Text, Tuple, TypeVar, overload
 
 _T = TypeVar("_T")
 
@@ -14,7 +14,7 @@ sep: str
 if sys.platform == "win32":
     altsep: str
 else:
-    altsep: Optional[str]
+    altsep: str | None
 extsep: str
 pathsep: str
 defpath: str
@@ -68,9 +68,9 @@ def join(__p1: bytes, __p2: Text, *p: Text) -> Text: ...
 @overload
 def join(__p1: Text, *p: Text) -> Text: ...
 @overload
-def relpath(path: str, start: Optional[str] = ...) -> str: ...
+def relpath(path: str, start: str | None = ...) -> str: ...
 @overload
-def relpath(path: Text, start: Optional[Text] = ...) -> Text: ...
+def relpath(path: Text, start: Text | None = ...) -> Text: ...
 def samefile(f1: Text, f2: Text) -> bool: ...
 def sameopenfile(fp1: int, fp2: int) -> bool: ...
 def samestat(s1: os.stat_result, s2: os.stat_result) -> bool: ...
diff --git a/stdlib/@python2/pprint.pyi b/stdlib/@python2/pprint.pyi
index bdf750407d12..407a9afb8e47 100644
--- a/stdlib/@python2/pprint.pyi
+++ b/stdlib/@python2/pprint.pyi
@@ -1,17 +1,15 @@
-from typing import IO, Any, Dict, Optional, Tuple
+from typing import IO, Any, Dict, Tuple
 
-def pformat(object: object, indent: int = ..., width: int = ..., depth: Optional[int] = ...) -> str: ...
+def pformat(object: object, indent: int = ..., width: int = ..., depth: int | None = ...) -> str: ...
 def pprint(
-    object: object, stream: Optional[IO[str]] = ..., indent: int = ..., width: int = ..., depth: Optional[int] = ...
+    object: object, stream: IO[str] | None = ..., indent: int = ..., width: int = ..., depth: int | None = ...
 ) -> None: ...
 def isreadable(object: object) -> bool: ...
 def isrecursive(object: object) -> bool: ...
 def saferepr(object: object) -> str: ...
 
 class PrettyPrinter:
-    def __init__(
-        self, indent: int = ..., width: int = ..., depth: Optional[int] = ..., stream: Optional[IO[str]] = ...
-    ) -> None: ...
+    def __init__(self, indent: int = ..., width: int = ..., depth: int | None = ..., stream: IO[str] | None = ...) -> None: ...
     def pformat(self, object: object) -> str: ...
     def pprint(self, object: object) -> None: ...
     def isreadable(self, object: object) -> bool: ...
diff --git a/stdlib/@python2/profile.pyi b/stdlib/@python2/profile.pyi
index e799c6b36e2f..08e9b906dd0d 100644
--- a/stdlib/@python2/profile.pyi
+++ b/stdlib/@python2/profile.pyi
@@ -1,8 +1,8 @@
-from typing import Any, Callable, Dict, Optional, Text, Tuple, TypeVar, Union
+from typing import Any, Callable, Dict, Text, Tuple, TypeVar
 
-def run(statement: str, filename: Optional[str] = ..., sort: Union[str, int] = ...) -> None: ...
+def run(statement: str, filename: str | None = ..., sort: str | int = ...) -> None: ...
 def runctx(
-    statement: str, globals: Dict[str, Any], locals: Dict[str, Any], filename: Optional[str] = ..., sort: Union[str, int] = ...
+    statement: str, globals: Dict[str, Any], locals: Dict[str, Any], filename: str | None = ..., sort: str | int = ...
 ) -> None: ...
 
 _SelfT = TypeVar("_SelfT", bound=Profile)
@@ -12,11 +12,11 @@ _Label = Tuple[str, int, str]
 class Profile:
     bias: int
     stats: dict[_Label, tuple[int, int, int, int, dict[_Label, tuple[int, int, int, int]]]]  # undocumented
-    def __init__(self, timer: Optional[Callable[[], float]] = ..., bias: Optional[int] = ...) -> None: ...
+    def __init__(self, timer: Callable[[], float] | None = ..., bias: int | None = ...) -> None: ...
     def set_cmd(self, cmd: str) -> None: ...
     def simulate_call(self, name: str) -> None: ...
     def simulate_cmd_complete(self) -> None: ...
-    def print_stats(self, sort: Union[str, int] = ...) -> None: ...
+    def print_stats(self, sort: str | int = ...) -> None: ...
     def dump_stats(self, file: Text) -> None: ...
     def create_stats(self) -> None: ...
     def snapshot_stats(self) -> None: ...
diff --git a/stdlib/@python2/pstats.pyi b/stdlib/@python2/pstats.pyi
index d1404dc7c01a..cecd1e84e305 100644
--- a/stdlib/@python2/pstats.pyi
+++ b/stdlib/@python2/pstats.pyi
@@ -1,6 +1,6 @@
 from cProfile import Profile as _cProfile
 from profile import Profile
-from typing import IO, Any, Dict, Iterable, List, Optional, Text, Tuple, TypeVar, Union, overload
+from typing import IO, Any, Dict, Iterable, List, Text, Tuple, TypeVar, Union, overload
 
 _Selector = Union[str, float, int]
 _T = TypeVar("_T", bound=Stats)
@@ -9,14 +9,14 @@ class Stats:
     sort_arg_dict_default: Dict[str, Tuple[Any, str]]
     def __init__(
         self: _T,
-        __arg: Union[None, str, Text, Profile, _cProfile] = ...,
-        *args: Union[None, str, Text, Profile, _cProfile, _T],
-        stream: Optional[IO[Any]] = ...,
+        __arg: None | str | Text | Profile | _cProfile = ...,
+        *args: None | str | Text | Profile | _cProfile | _T,
+        stream: IO[Any] | None = ...,
     ) -> None: ...
-    def init(self, arg: Union[None, str, Text, Profile, _cProfile]) -> None: ...
-    def load_stats(self, arg: Union[None, str, Text, Profile, _cProfile]) -> None: ...
+    def init(self, arg: None | str | Text | Profile | _cProfile) -> None: ...
+    def load_stats(self, arg: None | str | Text | Profile | _cProfile) -> None: ...
     def get_top_level_stats(self) -> None: ...
-    def add(self: _T, *arg_list: Union[None, str, Text, Profile, _cProfile, _T]) -> _T: ...
+    def add(self: _T, *arg_list: None | str | Text | Profile | _cProfile | _T) -> _T: ...
     def dump_stats(self, filename: Text) -> None: ...
     def get_sort_arg_defs(self) -> Dict[str, Tuple[Tuple[Tuple[int, int], ...], str]]: ...
     @overload
diff --git a/stdlib/@python2/pty.pyi b/stdlib/@python2/pty.pyi
index 93983690fff4..e8afa2df5166 100644
--- a/stdlib/@python2/pty.pyi
+++ b/stdlib/@python2/pty.pyi
@@ -1,4 +1,4 @@
-from typing import Callable, Iterable, Tuple, Union
+from typing import Callable, Iterable, Tuple
 
 _Reader = Callable[[int], bytes]
 
@@ -12,4 +12,4 @@ def openpty() -> Tuple[int, int]: ...
 def master_open() -> Tuple[int, str]: ...
 def slave_open(tty_name: str) -> int: ...
 def fork() -> Tuple[int, int]: ...
-def spawn(argv: Union[str, Iterable[str]], master_read: _Reader = ..., stdin_read: _Reader = ...) -> None: ...
+def spawn(argv: str | Iterable[str], master_read: _Reader = ..., stdin_read: _Reader = ...) -> None: ...
diff --git a/stdlib/@python2/py_compile.pyi b/stdlib/@python2/py_compile.pyi
index 94a8ace8e69a..44905b43da33 100644
--- a/stdlib/@python2/py_compile.pyi
+++ b/stdlib/@python2/py_compile.pyi
@@ -1,4 +1,4 @@
-from typing import List, Optional, Text, Type, Union
+from typing import List, Text, Type, Union
 
 _EitherStr = Union[bytes, Text]
 
@@ -9,7 +9,5 @@ class PyCompileError(Exception):
     msg: str
     def __init__(self, exc_type: Type[BaseException], exc_value: BaseException, file: str, msg: str = ...) -> None: ...
 
-def compile(
-    file: _EitherStr, cfile: Optional[_EitherStr] = ..., dfile: Optional[_EitherStr] = ..., doraise: bool = ...
-) -> None: ...
-def main(args: Optional[List[Text]] = ...) -> int: ...
+def compile(file: _EitherStr, cfile: _EitherStr | None = ..., dfile: _EitherStr | None = ..., doraise: bool = ...) -> None: ...
+def main(args: List[Text] | None = ...) -> int: ...
diff --git a/stdlib/@python2/pyclbr.pyi b/stdlib/@python2/pyclbr.pyi
index 855a2963c453..893079901665 100644
--- a/stdlib/@python2/pyclbr.pyi
+++ b/stdlib/@python2/pyclbr.pyi
@@ -1,13 +1,13 @@
-from typing import Dict, List, Optional, Sequence, Union
+from typing import Dict, List, Sequence
 
 class Class:
     module: str
     name: str
-    super: Optional[List[Union[Class, str]]]
+    super: List[Class | str] | None
     methods: Dict[str, int]
     file: int
     lineno: int
-    def __init__(self, module: str, name: str, super: Optional[List[Union[Class, str]]], file: str, lineno: int) -> None: ...
+    def __init__(self, module: str, name: str, super: List[Class | str] | None, file: str, lineno: int) -> None: ...
 
 class Function:
     module: str
@@ -16,5 +16,5 @@ class Function:
     lineno: int
     def __init__(self, module: str, name: str, file: str, lineno: int) -> None: ...
 
-def readmodule(module: str, path: Optional[Sequence[str]] = ...) -> Dict[str, Class]: ...
-def readmodule_ex(module: str, path: Optional[Sequence[str]] = ...) -> Dict[str, Union[Class, Function, List[str]]]: ...
+def readmodule(module: str, path: Sequence[str] | None = ...) -> Dict[str, Class]: ...
+def readmodule_ex(module: str, path: Sequence[str] | None = ...) -> Dict[str, Class | Function | List[str]]: ...
diff --git a/stdlib/@python2/pydoc.pyi b/stdlib/@python2/pydoc.pyi
index 857ed5a82c63..dee0c4710b39 100644
--- a/stdlib/@python2/pydoc.pyi
+++ b/stdlib/@python2/pydoc.pyi
@@ -15,7 +15,6 @@ from typing import (
     Text,
     Tuple,
     Type,
-    Union,
 )
 
 from repr import Repr
@@ -37,17 +36,17 @@ def replace(text: AnyStr, *pairs: AnyStr) -> AnyStr: ...
 def cram(text: str, maxlen: int) -> str: ...
 def stripid(text: str) -> str: ...
 def allmethods(cl: type) -> MutableMapping[str, MethodType]: ...
-def visiblename(name: str, all: Optional[Container[str]] = ..., obj: Optional[object] = ...) -> bool: ...
+def visiblename(name: str, all: Container[str] | None = ..., obj: object | None = ...) -> bool: ...
 def classify_class_attrs(object: object) -> List[Tuple[str, str, type, str]]: ...
 def ispackage(path: str) -> bool: ...
-def source_synopsis(file: IO[AnyStr]) -> Optional[AnyStr]: ...
-def synopsis(filename: str, cache: MutableMapping[str, Tuple[int, str]] = ...) -> Optional[str]: ...
+def source_synopsis(file: IO[AnyStr]) -> AnyStr | None: ...
+def synopsis(filename: str, cache: MutableMapping[str, Tuple[int, str]] = ...) -> str | None: ...
 
 class ErrorDuringImport(Exception):
     filename: str
-    exc: Optional[Type[BaseException]]
-    value: Optional[BaseException]
-    tb: Optional[TracebackType]
+    exc: Type[BaseException] | None
+    value: BaseException | None
+    tb: TracebackType | None
     def __init__(self, filename: str, exc_info: _Exc_Info) -> None: ...
 
 def importfile(path: str) -> ModuleType: ...
@@ -55,15 +54,15 @@ def safeimport(path: str, forceload: bool = ..., cache: MutableMapping[str, Modu
 
 class Doc:
     PYTHONDOCS: str
-    def document(self, object: object, name: Optional[str] = ..., *args: Any) -> str: ...
-    def fail(self, object: object, name: Optional[str] = ..., *args: Any) -> NoReturn: ...
-    def docmodule(self, object: object, name: Optional[str] = ..., *args: Any) -> str: ...
-    def docclass(self, object: object, name: Optional[str] = ..., *args: Any) -> str: ...
-    def docroutine(self, object: object, name: Optional[str] = ..., *args: Any) -> str: ...
-    def docother(self, object: object, name: Optional[str] = ..., *args: Any) -> str: ...
-    def docproperty(self, object: object, name: Optional[str] = ..., *args: Any) -> str: ...
-    def docdata(self, object: object, name: Optional[str] = ..., *args: Any) -> str: ...
-    def getdocloc(self, object: object, basedir: str = ...) -> Optional[str]: ...
+    def document(self, object: object, name: str | None = ..., *args: Any) -> str: ...
+    def fail(self, object: object, name: str | None = ..., *args: Any) -> NoReturn: ...
+    def docmodule(self, object: object, name: str | None = ..., *args: Any) -> str: ...
+    def docclass(self, object: object, name: str | None = ..., *args: Any) -> str: ...
+    def docroutine(self, object: object, name: str | None = ..., *args: Any) -> str: ...
+    def docother(self, object: object, name: str | None = ..., *args: Any) -> str: ...
+    def docproperty(self, object: object, name: str | None = ..., *args: Any) -> str: ...
+    def docdata(self, object: object, name: str | None = ..., *args: Any) -> str: ...
+    def getdocloc(self, object: object, basedir: str = ...) -> str | None: ...
 
 class HTMLRepr(Repr):
     maxlist: int
@@ -93,7 +92,7 @@ class HTMLDoc(Doc):
         contents: str,
         width: int = ...,
         prelude: str = ...,
-        marginalia: Optional[str] = ...,
+        marginalia: str | None = ...,
         gap: str = ...,
     ) -> str: ...
     def bigsection(self, title: str, *args: Any) -> str: ...
@@ -107,20 +106,20 @@ class HTMLDoc(Doc):
     def markup(
         self,
         text: str,
-        escape: Optional[Callable[[str], str]] = ...,
+        escape: Callable[[str], str] | None = ...,
         funcs: Mapping[str, str] = ...,
         classes: Mapping[str, str] = ...,
         methods: Mapping[str, str] = ...,
     ) -> str: ...
     def formattree(
-        self, tree: List[Union[Tuple[type, Tuple[type, ...]], List[Any]]], modname: str, parent: Optional[type] = ...
+        self, tree: List[Tuple[type, Tuple[type, ...]] | List[Any]], modname: str, parent: type | None = ...
     ) -> str: ...
-    def docmodule(self, object: object, name: Optional[str] = ..., mod: Optional[str] = ..., *ignored: Any) -> str: ...
+    def docmodule(self, object: object, name: str | None = ..., mod: str | None = ..., *ignored: Any) -> str: ...
     def docclass(
         self,
         object: object,
-        name: Optional[str] = ...,
-        mod: Optional[str] = ...,
+        name: str | None = ...,
+        mod: str | None = ...,
         funcs: Mapping[str, str] = ...,
         classes: Mapping[str, str] = ...,
         *ignored: Any,
@@ -129,22 +128,22 @@ class HTMLDoc(Doc):
     def docroutine(
         self,
         object: object,
-        name: Optional[str] = ...,
-        mod: Optional[str] = ...,
+        name: str | None = ...,
+        mod: str | None = ...,
         funcs: Mapping[str, str] = ...,
         classes: Mapping[str, str] = ...,
         methods: Mapping[str, str] = ...,
-        cl: Optional[type] = ...,
+        cl: type | None = ...,
         *ignored: Any,
     ) -> str: ...
     def docproperty(
-        self, object: object, name: Optional[str] = ..., mod: Optional[str] = ..., cl: Optional[Any] = ..., *ignored: Any
+        self, object: object, name: str | None = ..., mod: str | None = ..., cl: Any | None = ..., *ignored: Any
     ) -> str: ...
-    def docother(self, object: object, name: Optional[str] = ..., mod: Optional[Any] = ..., *ignored: Any) -> str: ...
+    def docother(self, object: object, name: str | None = ..., mod: Any | None = ..., *ignored: Any) -> str: ...
     def docdata(
-        self, object: object, name: Optional[str] = ..., mod: Optional[Any] = ..., cl: Optional[Any] = ..., *ignored: Any
+        self, object: object, name: str | None = ..., mod: Any | None = ..., cl: Any | None = ..., *ignored: Any
     ) -> str: ...
-    def index(self, dir: str, shadowed: Optional[MutableMapping[str, bool]] = ...) -> str: ...
+    def index(self, dir: str, shadowed: MutableMapping[str, bool] | None = ...) -> str: ...
     def filelink(self, url: str, path: str) -> str: ...
 
 class TextRepr(Repr):
@@ -165,32 +164,28 @@ class TextDoc(Doc):
     def indent(self, text: str, prefix: str = ...) -> str: ...
     def section(self, title: str, contents: str) -> str: ...
     def formattree(
-        self,
-        tree: List[Union[Tuple[type, Tuple[type, ...]], List[Any]]],
-        modname: str,
-        parent: Optional[type] = ...,
-        prefix: str = ...,
+        self, tree: List[Tuple[type, Tuple[type, ...]] | List[Any]], modname: str, parent: type | None = ..., prefix: str = ...
     ) -> str: ...
-    def docmodule(self, object: object, name: Optional[str] = ..., mod: Optional[Any] = ..., *ignored: Any) -> str: ...
-    def docclass(self, object: object, name: Optional[str] = ..., mod: Optional[str] = ..., *ignored: Any) -> str: ...
+    def docmodule(self, object: object, name: str | None = ..., mod: Any | None = ..., *ignored: Any) -> str: ...
+    def docclass(self, object: object, name: str | None = ..., mod: str | None = ..., *ignored: Any) -> str: ...
     def formatvalue(self, object: object) -> str: ...
     def docroutine(
-        self, object: object, name: Optional[str] = ..., mod: Optional[str] = ..., cl: Optional[Any] = ..., *ignored: Any
+        self, object: object, name: str | None = ..., mod: str | None = ..., cl: Any | None = ..., *ignored: Any
     ) -> str: ...
     def docproperty(
-        self, object: object, name: Optional[str] = ..., mod: Optional[Any] = ..., cl: Optional[Any] = ..., *ignored: Any
+        self, object: object, name: str | None = ..., mod: Any | None = ..., cl: Any | None = ..., *ignored: Any
     ) -> str: ...
     def docdata(
-        self, object: object, name: Optional[str] = ..., mod: Optional[str] = ..., cl: Optional[Any] = ..., *ignored: Any
+        self, object: object, name: str | None = ..., mod: str | None = ..., cl: Any | None = ..., *ignored: Any
     ) -> str: ...
     def docother(
         self,
         object: object,
-        name: Optional[str] = ...,
-        mod: Optional[str] = ...,
-        parent: Optional[str] = ...,
-        maxlen: Optional[int] = ...,
-        doc: Optional[Any] = ...,
+        name: str | None = ...,
+        mod: str | None = ...,
+        parent: str | None = ...,
+        maxlen: int | None = ...,
+        doc: Any | None = ...,
         *ignored: Any,
     ) -> str: ...
 
@@ -209,22 +204,20 @@ html: HTMLDoc
 
 class _OldStyleClass: ...
 
-def resolve(thing: Union[str, object], forceload: bool = ...) -> Optional[Tuple[object, str]]: ...
-def render_doc(thing: Union[str, object], title: str = ..., forceload: bool = ..., renderer: Optional[Doc] = ...) -> str: ...
-def doc(
-    thing: Union[str, object], title: str = ..., forceload: bool = ..., output: Optional[SupportsWrite[str]] = ...
-) -> None: ...
-def writedoc(thing: Union[str, object], forceload: bool = ...) -> None: ...
-def writedocs(dir: str, pkgpath: str = ..., done: Optional[Any] = ...) -> None: ...
+def resolve(thing: str | object, forceload: bool = ...) -> Tuple[object, str] | None: ...
+def render_doc(thing: str | object, title: str = ..., forceload: bool = ..., renderer: Doc | None = ...) -> str: ...
+def doc(thing: str | object, title: str = ..., forceload: bool = ..., output: SupportsWrite[str] | None = ...) -> None: ...
+def writedoc(thing: str | object, forceload: bool = ...) -> None: ...
+def writedocs(dir: str, pkgpath: str = ..., done: Any | None = ...) -> None: ...
 
 class Helper:
-    keywords: Dict[str, Union[str, Tuple[str, str]]]
+    keywords: Dict[str, str | Tuple[str, str]]
     symbols: Dict[str, str]
-    topics: Dict[str, Union[str, Tuple[str, ...]]]
-    def __init__(self, input: Optional[IO[str]] = ..., output: Optional[IO[str]] = ...) -> None: ...
+    topics: Dict[str, str | Tuple[str, ...]]
+    def __init__(self, input: IO[str] | None = ..., output: IO[str] | None = ...) -> None: ...
     input: IO[str]
     output: IO[str]
-    def __call__(self, request: Union[str, Helper, object] = ...) -> None: ...
+    def __call__(self, request: str | Helper | object = ...) -> None: ...
     def interact(self) -> None: ...
     def getline(self, prompt: str) -> str: ...
     def help(self, request: Any) -> None: ...
@@ -252,14 +245,14 @@ class ModuleScanner:
     quit: bool
     def run(
         self,
-        callback: Callable[[Optional[str], str, str], None],
-        key: Optional[Any] = ...,
-        completer: Optional[Callable[[], None]] = ...,
-        onerror: Optional[Callable[[str], None]] = ...,
+        callback: Callable[[str | None, str, str], None],
+        key: Any | None = ...,
+        completer: Callable[[], None] | None = ...,
+        onerror: Callable[[str], None] | None = ...,
     ) -> None: ...
 
 def apropos(key: str) -> None: ...
 def ispath(x: Any) -> bool: ...
 def cli() -> None: ...
-def serve(port: int, callback: Optional[Callable[[Any], None]] = ..., completer: Optional[Callable[[], None]] = ...) -> None: ...
+def serve(port: int, callback: Callable[[Any], None] | None = ..., completer: Callable[[], None] | None = ...) -> None: ...
 def gui() -> None: ...
diff --git a/stdlib/@python2/pyexpat/__init__.pyi b/stdlib/@python2/pyexpat/__init__.pyi
index 65f6b0e9f7de..bd73f850b559 100644
--- a/stdlib/@python2/pyexpat/__init__.pyi
+++ b/stdlib/@python2/pyexpat/__init__.pyi
@@ -1,7 +1,7 @@
 import pyexpat.errors as errors
 import pyexpat.model as model
 from _typeshed import SupportsRead
-from typing import Any, Callable, Dict, List, Optional, Text, Tuple, Union
+from typing import Any, Callable, Dict, List, Optional, Text, Tuple
 
 EXPAT_VERSION: str  # undocumented
 version_info: Tuple[int, int, int]  # undocumented
@@ -22,12 +22,12 @@ XML_PARAM_ENTITY_PARSING_ALWAYS: int
 _Model = Tuple[int, int, Optional[str], Tuple[Any, ...]]
 
 class XMLParserType(object):
-    def Parse(self, __data: Union[Text, bytes], __isfinal: bool = ...) -> int: ...
+    def Parse(self, __data: Text | bytes, __isfinal: bool = ...) -> int: ...
     def ParseFile(self, __file: SupportsRead[bytes]) -> int: ...
     def SetBase(self, __base: Text) -> None: ...
-    def GetBase(self) -> Optional[str]: ...
-    def GetInputContext(self) -> Optional[bytes]: ...
-    def ExternalEntityParserCreate(self, __context: Optional[Text], __encoding: Text = ...) -> XMLParserType: ...
+    def GetBase(self) -> str | None: ...
+    def GetInputContext(self) -> bytes | None: ...
+    def ExternalEntityParserCreate(self, __context: Text | None, __encoding: Text = ...) -> XMLParserType: ...
     def SetParamEntityParsing(self, __flag: int) -> int: ...
     def UseForeignDTD(self, __flag: bool = ...) -> None: ...
     buffer_size: int
@@ -43,37 +43,33 @@ class XMLParserType(object):
     CurrentByteIndex: int
     CurrentColumnNumber: int
     CurrentLineNumber: int
-    XmlDeclHandler: Optional[Callable[[str, Optional[str], int], Any]]
-    StartDoctypeDeclHandler: Optional[Callable[[str, Optional[str], Optional[str], bool], Any]]
-    EndDoctypeDeclHandler: Optional[Callable[[], Any]]
-    ElementDeclHandler: Optional[Callable[[str, _Model], Any]]
-    AttlistDeclHandler: Optional[Callable[[str, str, str, Optional[str], bool], Any]]
-    StartElementHandler: Optional[
-        Union[
-            Callable[[str, Dict[str, str]], Any],
-            Callable[[str, List[str]], Any],
-            Callable[[str, Union[Dict[str, str]], List[str]], Any],
-        ]
-    ]
-    EndElementHandler: Optional[Callable[[str], Any]]
-    ProcessingInstructionHandler: Optional[Callable[[str, str], Any]]
-    CharacterDataHandler: Optional[Callable[[str], Any]]
-    UnparsedEntityDeclHandler: Optional[Callable[[str, Optional[str], str, Optional[str], str], Any]]
-    EntityDeclHandler: Optional[Callable[[str, bool, Optional[str], Optional[str], str, Optional[str], Optional[str]], Any]]
-    NotationDeclHandler: Optional[Callable[[str, Optional[str], str, Optional[str]], Any]]
-    StartNamespaceDeclHandler: Optional[Callable[[str, str], Any]]
-    EndNamespaceDeclHandler: Optional[Callable[[str], Any]]
-    CommentHandler: Optional[Callable[[str], Any]]
-    StartCdataSectionHandler: Optional[Callable[[], Any]]
-    EndCdataSectionHandler: Optional[Callable[[], Any]]
-    DefaultHandler: Optional[Callable[[str], Any]]
-    DefaultHandlerExpand: Optional[Callable[[str], Any]]
-    NotStandaloneHandler: Optional[Callable[[], int]]
-    ExternalEntityRefHandler: Optional[Callable[[str, Optional[str], Optional[str], Optional[str]], int]]
+    XmlDeclHandler: Callable[[str, str | None, int], Any] | None
+    StartDoctypeDeclHandler: Callable[[str, str | None, str | None, bool], Any] | None
+    EndDoctypeDeclHandler: Callable[[], Any] | None
+    ElementDeclHandler: Callable[[str, _Model], Any] | None
+    AttlistDeclHandler: Callable[[str, str, str, str | None, bool], Any] | None
+    StartElementHandler: Callable[[str, Dict[str, str]], Any] | Callable[[str, List[str]], Any] | Callable[
+        [str, Dict[str, str], List[str]], Any
+    ] | None
+    EndElementHandler: Callable[[str], Any] | None
+    ProcessingInstructionHandler: Callable[[str, str], Any] | None
+    CharacterDataHandler: Callable[[str], Any] | None
+    UnparsedEntityDeclHandler: Callable[[str, str | None, str, str | None, str], Any] | None
+    EntityDeclHandler: Callable[[str, bool, str | None, str | None, str, str | None, str | None], Any] | None
+    NotationDeclHandler: Callable[[str, str | None, str, str | None], Any] | None
+    StartNamespaceDeclHandler: Callable[[str, str], Any] | None
+    EndNamespaceDeclHandler: Callable[[str], Any] | None
+    CommentHandler: Callable[[str], Any] | None
+    StartCdataSectionHandler: Callable[[], Any] | None
+    EndCdataSectionHandler: Callable[[], Any] | None
+    DefaultHandler: Callable[[str], Any] | None
+    DefaultHandlerExpand: Callable[[str], Any] | None
+    NotStandaloneHandler: Callable[[], int] | None
+    ExternalEntityRefHandler: Callable[[str, str | None, str | None, str | None], int] | None
 
 def ErrorString(__code: int) -> str: ...
 
 # intern is undocumented
 def ParserCreate(
-    encoding: Optional[Text] = ..., namespace_separator: Optional[Text] = ..., intern: Optional[Dict[str, Any]] = ...
+    encoding: Text | None = ..., namespace_separator: Text | None = ..., intern: Dict[str, Any] | None = ...
 ) -> XMLParserType: ...
diff --git a/stdlib/@python2/re.pyi b/stdlib/@python2/re.pyi
index aa770b6b64be..fbe021ce67be 100644
--- a/stdlib/@python2/re.pyi
+++ b/stdlib/@python2/re.pyi
@@ -1,4 +1,4 @@
-from typing import Any, AnyStr, Callable, Iterator, List, Match, Optional, Pattern, Tuple, Union, overload
+from typing import Any, AnyStr, Callable, Iterator, List, Match, Pattern, Tuple, overload
 
 # ----- re variables and constants -----
 DEBUG: int
@@ -24,65 +24,59 @@ def compile(pattern: AnyStr, flags: int = ...) -> Pattern[AnyStr]: ...
 @overload
 def compile(pattern: Pattern[AnyStr], flags: int = ...) -> Pattern[AnyStr]: ...
 @overload
-def search(pattern: Union[str, unicode], string: AnyStr, flags: int = ...) -> Optional[Match[AnyStr]]: ...
+def search(pattern: str | unicode, string: AnyStr, flags: int = ...) -> Match[AnyStr] | None: ...
 @overload
-def search(pattern: Union[Pattern[str], Pattern[unicode]], string: AnyStr, flags: int = ...) -> Optional[Match[AnyStr]]: ...
+def search(pattern: Pattern[str] | Pattern[unicode], string: AnyStr, flags: int = ...) -> Match[AnyStr] | None: ...
 @overload
-def match(pattern: Union[str, unicode], string: AnyStr, flags: int = ...) -> Optional[Match[AnyStr]]: ...
+def match(pattern: str | unicode, string: AnyStr, flags: int = ...) -> Match[AnyStr] | None: ...
 @overload
-def match(pattern: Union[Pattern[str], Pattern[unicode]], string: AnyStr, flags: int = ...) -> Optional[Match[AnyStr]]: ...
+def match(pattern: Pattern[str] | Pattern[unicode], string: AnyStr, flags: int = ...) -> Match[AnyStr] | None: ...
 @overload
-def split(pattern: Union[str, unicode], string: AnyStr, maxsplit: int = ..., flags: int = ...) -> List[AnyStr]: ...
+def split(pattern: str | unicode, string: AnyStr, maxsplit: int = ..., flags: int = ...) -> List[AnyStr]: ...
 @overload
-def split(
-    pattern: Union[Pattern[str], Pattern[unicode]], string: AnyStr, maxsplit: int = ..., flags: int = ...
-) -> List[AnyStr]: ...
+def split(pattern: Pattern[str] | Pattern[unicode], string: AnyStr, maxsplit: int = ..., flags: int = ...) -> List[AnyStr]: ...
 @overload
-def findall(pattern: Union[str, unicode], string: AnyStr, flags: int = ...) -> List[Any]: ...
+def findall(pattern: str | unicode, string: AnyStr, flags: int = ...) -> List[Any]: ...
 @overload
-def findall(pattern: Union[Pattern[str], Pattern[unicode]], string: AnyStr, flags: int = ...) -> List[Any]: ...
+def findall(pattern: Pattern[str] | Pattern[unicode], string: AnyStr, flags: int = ...) -> List[Any]: ...
 
 # Return an iterator yielding match objects over all non-overlapping matches
 # for the RE pattern in string. The string is scanned left-to-right, and
 # matches are returned in the order found. Empty matches are included in the
 # result unless they touch the beginning of another match.
 @overload
-def finditer(pattern: Union[str, unicode], string: AnyStr, flags: int = ...) -> Iterator[Match[AnyStr]]: ...
+def finditer(pattern: str | unicode, string: AnyStr, flags: int = ...) -> Iterator[Match[AnyStr]]: ...
 @overload
-def finditer(pattern: Union[Pattern[str], Pattern[unicode]], string: AnyStr, flags: int = ...) -> Iterator[Match[AnyStr]]: ...
+def finditer(pattern: Pattern[str] | Pattern[unicode], string: AnyStr, flags: int = ...) -> Iterator[Match[AnyStr]]: ...
 @overload
-def sub(pattern: Union[str, unicode], repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...) -> AnyStr: ...
+def sub(pattern: str | unicode, repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...) -> AnyStr: ...
 @overload
 def sub(
-    pattern: Union[str, unicode], repl: Callable[[Match[AnyStr]], AnyStr], string: AnyStr, count: int = ..., flags: int = ...
+    pattern: str | unicode, repl: Callable[[Match[AnyStr]], AnyStr], string: AnyStr, count: int = ..., flags: int = ...
 ) -> AnyStr: ...
 @overload
-def sub(
-    pattern: Union[Pattern[str], Pattern[unicode]], repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...
-) -> AnyStr: ...
+def sub(pattern: Pattern[str] | Pattern[unicode], repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...) -> AnyStr: ...
 @overload
 def sub(
-    pattern: Union[Pattern[str], Pattern[unicode]],
+    pattern: Pattern[str] | Pattern[unicode],
     repl: Callable[[Match[AnyStr]], AnyStr],
     string: AnyStr,
     count: int = ...,
     flags: int = ...,
 ) -> AnyStr: ...
 @overload
-def subn(
-    pattern: Union[str, unicode], repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...
-) -> Tuple[AnyStr, int]: ...
+def subn(pattern: str | unicode, repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...) -> Tuple[AnyStr, int]: ...
 @overload
 def subn(
-    pattern: Union[str, unicode], repl: Callable[[Match[AnyStr]], AnyStr], string: AnyStr, count: int = ..., flags: int = ...
+    pattern: str | unicode, repl: Callable[[Match[AnyStr]], AnyStr], string: AnyStr, count: int = ..., flags: int = ...
 ) -> Tuple[AnyStr, int]: ...
 @overload
 def subn(
-    pattern: Union[Pattern[str], Pattern[unicode]], repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...
+    pattern: Pattern[str] | Pattern[unicode], repl: AnyStr, string: AnyStr, count: int = ..., flags: int = ...
 ) -> Tuple[AnyStr, int]: ...
 @overload
 def subn(
-    pattern: Union[Pattern[str], Pattern[unicode]],
+    pattern: Pattern[str] | Pattern[unicode],
     repl: Callable[[Match[AnyStr]], AnyStr],
     string: AnyStr,
     count: int = ...,
@@ -90,4 +84,4 @@ def subn(
 ) -> Tuple[AnyStr, int]: ...
 def escape(string: AnyStr) -> AnyStr: ...
 def purge() -> None: ...
-def template(pattern: Union[AnyStr, Pattern[AnyStr]], flags: int = ...) -> Pattern[AnyStr]: ...
+def template(pattern: AnyStr | Pattern[AnyStr], flags: int = ...) -> Pattern[AnyStr]: ...
diff --git a/stdlib/@python2/readline.pyi b/stdlib/@python2/readline.pyi
index 579308f75bc1..fb9b12d9a8e9 100644
--- a/stdlib/@python2/readline.pyi
+++ b/stdlib/@python2/readline.pyi
@@ -4,12 +4,12 @@ _CompleterT = Optional[Callable[[str, int], Optional[str]]]
 _CompDispT = Optional[Callable[[str, Sequence[str], int], None]]
 
 def parse_and_bind(__string: str) -> None: ...
-def read_init_file(__filename: Optional[Text] = ...) -> None: ...
+def read_init_file(__filename: Text | None = ...) -> None: ...
 def get_line_buffer() -> str: ...
 def insert_text(__string: str) -> None: ...
 def redisplay() -> None: ...
-def read_history_file(__filename: Optional[Text] = ...) -> None: ...
-def write_history_file(__filename: Optional[Text] = ...) -> None: ...
+def read_history_file(__filename: Text | None = ...) -> None: ...
+def write_history_file(__filename: Text | None = ...) -> None: ...
 def get_history_length() -> int: ...
 def set_history_length(__length: int) -> None: ...
 def clear_history() -> None: ...
@@ -18,8 +18,8 @@ def get_history_item(__index: int) -> str: ...
 def remove_history_item(__pos: int) -> None: ...
 def replace_history_item(__pos: int, __line: str) -> None: ...
 def add_history(__string: str) -> None: ...
-def set_startup_hook(__function: Optional[Callable[[], None]] = ...) -> None: ...
-def set_pre_input_hook(__function: Optional[Callable[[], None]] = ...) -> None: ...
+def set_startup_hook(__function: Callable[[], None] | None = ...) -> None: ...
+def set_pre_input_hook(__function: Callable[[], None] | None = ...) -> None: ...
 def set_completer(__function: _CompleterT = ...) -> None: ...
 def get_completer() -> _CompleterT: ...
 def get_completion_type() -> int: ...
diff --git a/stdlib/@python2/rfc822.pyi b/stdlib/@python2/rfc822.pyi
index f536568b807d..d6ae0031ffdf 100644
--- a/stdlib/@python2/rfc822.pyi
+++ b/stdlib/@python2/rfc822.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Optional
+from typing import Any
 
 class Message:
     fp: Any
@@ -18,7 +18,7 @@ class Message:
     def getallmatchingheaders(self, name): ...
     def getfirstmatchingheader(self, name): ...
     def getrawheader(self, name): ...
-    def getheader(self, name, default: Optional[Any] = ...): ...
+    def getheader(self, name, default: Any | None = ...): ...
     get: Any
     def getheaders(self, name): ...
     def getaddr(self, name): ...
@@ -57,7 +57,7 @@ class AddrlistClass:
     def getquote(self): ...
     def getcomment(self): ...
     def getdomainliteral(self): ...
-    def getatom(self, atomends: Optional[Any] = ...): ...
+    def getatom(self, atomends: Any | None = ...): ...
     def getphraselist(self): ...
 
 class AddressList(AddrlistClass):
diff --git a/stdlib/@python2/rlcompleter.pyi b/stdlib/@python2/rlcompleter.pyi
index a542c45c979b..a61c61eb24f2 100644
--- a/stdlib/@python2/rlcompleter.pyi
+++ b/stdlib/@python2/rlcompleter.pyi
@@ -1,7 +1,7 @@
-from typing import Any, Dict, Optional, Union
+from typing import Any, Dict, Union
 
 _Text = Union[str, unicode]
 
 class Completer:
-    def __init__(self, namespace: Optional[Dict[str, Any]] = ...) -> None: ...
-    def complete(self, text: _Text, state: int) -> Optional[str]: ...
+    def __init__(self, namespace: Dict[str, Any] | None = ...) -> None: ...
+    def complete(self, text: _Text, state: int) -> str | None: ...
diff --git a/stdlib/@python2/runpy.pyi b/stdlib/@python2/runpy.pyi
index 6674af077d5d..3d5f0500f2e0 100644
--- a/stdlib/@python2/runpy.pyi
+++ b/stdlib/@python2/runpy.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Optional
+from typing import Any
 
 class _TempModule:
     mod_name: Any
@@ -13,5 +13,5 @@ class _ModifiedArgv0:
     def __enter__(self): ...
     def __exit__(self, *args): ...
 
-def run_module(mod_name, init_globals: Optional[Any] = ..., run_name: Optional[Any] = ..., alter_sys: bool = ...): ...
-def run_path(path_name, init_globals: Optional[Any] = ..., run_name: Optional[Any] = ...): ...
+def run_module(mod_name, init_globals: Any | None = ..., run_name: Any | None = ..., alter_sys: bool = ...): ...
+def run_path(path_name, init_globals: Any | None = ..., run_name: Any | None = ...): ...
diff --git a/stdlib/@python2/select.pyi b/stdlib/@python2/select.pyi
index 716c34a378ca..b960fd4e24b5 100644
--- a/stdlib/@python2/select.pyi
+++ b/stdlib/@python2/select.pyi
@@ -1,6 +1,6 @@
 import sys
 from _typeshed import FileDescriptorLike
-from typing import Any, Iterable, List, Optional, Tuple
+from typing import Any, Iterable, List, Tuple
 
 if sys.platform != "win32":
     PIPE_BUF: int
@@ -21,10 +21,10 @@ class poll:
     def register(self, fd: FileDescriptorLike, eventmask: int = ...) -> None: ...
     def modify(self, fd: FileDescriptorLike, eventmask: int) -> None: ...
     def unregister(self, fd: FileDescriptorLike) -> None: ...
-    def poll(self, timeout: Optional[float] = ...) -> List[Tuple[int, int]]: ...
+    def poll(self, timeout: float | None = ...) -> List[Tuple[int, int]]: ...
 
 def select(
-    __rlist: Iterable[Any], __wlist: Iterable[Any], __xlist: Iterable[Any], __timeout: Optional[float] = ...
+    __rlist: Iterable[Any], __wlist: Iterable[Any], __xlist: Iterable[Any], __timeout: float | None = ...
 ) -> Tuple[List[Any], List[Any], List[Any]]: ...
 
 class error(Exception): ...
@@ -53,7 +53,7 @@ if sys.platform != "linux" and sys.platform != "win32":
         def __init__(self) -> None: ...
         def close(self) -> None: ...
         def control(
-            self, __changelist: Optional[Iterable[kevent]], __maxevents: int, __timeout: Optional[float] = ...
+            self, __changelist: Iterable[kevent] | None, __maxevents: int, __timeout: float | None = ...
         ) -> List[kevent]: ...
         def fileno(self) -> int: ...
         @classmethod
@@ -106,7 +106,7 @@ if sys.platform == "linux":
         def register(self, fd: FileDescriptorLike, eventmask: int = ...) -> None: ...
         def modify(self, fd: FileDescriptorLike, eventmask: int) -> None: ...
         def unregister(self, fd: FileDescriptorLike) -> None: ...
-        def poll(self, timeout: Optional[float] = ..., maxevents: int = ...) -> List[Tuple[int, int]]: ...
+        def poll(self, timeout: float | None = ..., maxevents: int = ...) -> List[Tuple[int, int]]: ...
         @classmethod
         def fromfd(cls, __fd: FileDescriptorLike) -> epoll: ...
     EPOLLERR: int
diff --git a/stdlib/@python2/sets.pyi b/stdlib/@python2/sets.pyi
index 1ee3e8b26e1b..d2b94ea44bbc 100644
--- a/stdlib/@python2/sets.pyi
+++ b/stdlib/@python2/sets.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Hashable, Iterable, Iterator, MutableMapping, Optional, TypeVar, Union
+from typing import Any, Hashable, Iterable, Iterator, MutableMapping, TypeVar, Union
 
 _T = TypeVar("_T")
 _Setlike = Union[BaseSet[_T], Iterable[_T]]
@@ -33,11 +33,11 @@ class BaseSet(Iterable[_T]):
     def __gt__(self, other: BaseSet[_T]) -> bool: ...
 
 class ImmutableSet(BaseSet[_T], Hashable):
-    def __init__(self, iterable: Optional[_Setlike[_T]] = ...) -> None: ...
+    def __init__(self, iterable: _Setlike[_T] | None = ...) -> None: ...
     def __hash__(self) -> int: ...
 
 class Set(BaseSet[_T]):
-    def __init__(self, iterable: Optional[_Setlike[_T]] = ...) -> None: ...
+    def __init__(self, iterable: _Setlike[_T] | None = ...) -> None: ...
     def __ior__(self: _SelfT, other: BaseSet[_T]) -> _SelfT: ...
     def union_update(self, other: _Setlike[_T]) -> None: ...
     def __iand__(self: _SelfT, other: BaseSet[_T]) -> _SelfT: ...
diff --git a/stdlib/@python2/shelve.pyi b/stdlib/@python2/shelve.pyi
index 442c3fe3d52e..d9b1a00e58df 100644
--- a/stdlib/@python2/shelve.pyi
+++ b/stdlib/@python2/shelve.pyi
@@ -1,9 +1,9 @@
 import collections
-from typing import Any, Dict, Iterator, List, Optional, Tuple
+from typing import Any, Dict, Iterator, List, Tuple
 
 class Shelf(collections.MutableMapping[Any, Any]):
     def __init__(
-        self, dict: Dict[Any, Any], protocol: Optional[int] = ..., writeback: bool = ..., keyencoding: str = ...
+        self, dict: Dict[Any, Any], protocol: int | None = ..., writeback: bool = ..., keyencoding: str = ...
     ) -> None: ...
     def __iter__(self) -> Iterator[str]: ...
     def keys(self) -> List[Any]: ...
@@ -22,7 +22,7 @@ class Shelf(collections.MutableMapping[Any, Any]):
 
 class BsdDbShelf(Shelf):
     def __init__(
-        self, dict: Dict[Any, Any], protocol: Optional[int] = ..., writeback: bool = ..., keyencoding: str = ...
+        self, dict: Dict[Any, Any], protocol: int | None = ..., writeback: bool = ..., keyencoding: str = ...
     ) -> None: ...
     def set_location(self, key: Any) -> Tuple[str, Any]: ...
     def next(self) -> Tuple[str, Any]: ...
@@ -31,6 +31,6 @@ class BsdDbShelf(Shelf):
     def last(self) -> Tuple[str, Any]: ...
 
 class DbfilenameShelf(Shelf):
-    def __init__(self, filename: str, flag: str = ..., protocol: Optional[int] = ..., writeback: bool = ...) -> None: ...
+    def __init__(self, filename: str, flag: str = ..., protocol: int | None = ..., writeback: bool = ...) -> None: ...
 
-def open(filename: str, flag: str = ..., protocol: Optional[int] = ..., writeback: bool = ...) -> DbfilenameShelf: ...
+def open(filename: str, flag: str = ..., protocol: int | None = ..., writeback: bool = ...) -> DbfilenameShelf: ...
diff --git a/stdlib/@python2/shlex.pyi b/stdlib/@python2/shlex.pyi
index 37c667238f09..89c28fc9be7f 100644
--- a/stdlib/@python2/shlex.pyi
+++ b/stdlib/@python2/shlex.pyi
@@ -1,14 +1,14 @@
-from typing import IO, Any, List, Optional, Text, TypeVar, Union
+from typing import IO, Any, List, Text, TypeVar
 
-def split(s: Optional[str], comments: bool = ..., posix: bool = ...) -> List[str]: ...
+def split(s: str | None, comments: bool = ..., posix: bool = ...) -> List[str]: ...
 
 _SLT = TypeVar("_SLT", bound=shlex)
 
 class shlex:
-    def __init__(self, instream: Union[IO[Any], Text] = ..., infile: IO[Any] = ..., posix: bool = ...) -> None: ...
+    def __init__(self, instream: IO[Any] | Text = ..., infile: IO[Any] = ..., posix: bool = ...) -> None: ...
     def __iter__(self: _SLT) -> _SLT: ...
     def next(self) -> str: ...
-    def get_token(self) -> Optional[str]: ...
+    def get_token(self) -> str | None: ...
     def push_token(self, _str: str) -> None: ...
     def read_token(self) -> str: ...
     def sourcehook(self, filename: str) -> None: ...
@@ -23,8 +23,8 @@ class shlex:
     escapedquotes: str
     whitespace_split: bool
     infile: IO[Any]
-    source: Optional[str]
+    source: str | None
     debug: int
     lineno: int
     token: Any
-    eof: Optional[str]
+    eof: str | None
diff --git a/stdlib/@python2/shutil.pyi b/stdlib/@python2/shutil.pyi
index ff4467ffc471..4805c8e4cdb7 100644
--- a/stdlib/@python2/shutil.pyi
+++ b/stdlib/@python2/shutil.pyi
@@ -1,5 +1,5 @@
 from _typeshed import SupportsRead, SupportsWrite
-from typing import Any, AnyStr, Callable, Iterable, List, Optional, Sequence, Set, Text, Tuple, Type, TypeVar, Union
+from typing import Any, AnyStr, Callable, Iterable, List, Sequence, Set, Text, Tuple, Type, TypeVar, Union
 
 _AnyStr = TypeVar("_AnyStr", str, unicode)
 _AnyPath = TypeVar("_AnyPath", str, unicode)
@@ -17,9 +17,9 @@ def copy(src: Text, dst: Text) -> _PathReturn: ...
 def copy2(src: Text, dst: Text) -> _PathReturn: ...
 def ignore_patterns(*patterns: Text) -> Callable[[Any, List[_AnyStr]], Set[_AnyStr]]: ...
 def copytree(
-    src: AnyStr, dst: AnyStr, symlinks: bool = ..., ignore: Union[None, Callable[[AnyStr, List[AnyStr]], Iterable[AnyStr]]] = ...
+    src: AnyStr, dst: AnyStr, symlinks: bool = ..., ignore: None | Callable[[AnyStr, List[AnyStr]], Iterable[AnyStr]] = ...
 ) -> _PathReturn: ...
-def rmtree(path: _AnyPath, ignore_errors: bool = ..., onerror: Optional[Callable[[Any, _AnyPath, Any], Any]] = ...) -> None: ...
+def rmtree(path: _AnyPath, ignore_errors: bool = ..., onerror: Callable[[Any, _AnyPath, Any], Any] | None = ...) -> None: ...
 
 _CopyFn = Union[Callable[[str, str], None], Callable[[Text, Text], None]]
 
@@ -27,19 +27,19 @@ def move(src: Text, dst: Text) -> _PathReturn: ...
 def make_archive(
     base_name: _AnyStr,
     format: str,
-    root_dir: Optional[Text] = ...,
-    base_dir: Optional[Text] = ...,
+    root_dir: Text | None = ...,
+    base_dir: Text | None = ...,
     verbose: bool = ...,
     dry_run: bool = ...,
-    owner: Optional[str] = ...,
-    group: Optional[str] = ...,
-    logger: Optional[Any] = ...,
+    owner: str | None = ...,
+    group: str | None = ...,
+    logger: Any | None = ...,
 ) -> _AnyStr: ...
 def get_archive_formats() -> List[Tuple[str, str]]: ...
 def register_archive_format(
     name: str,
     function: Callable[..., Any],
-    extra_args: Optional[Sequence[Union[Tuple[str, Any], List[Any]]]] = ...,
+    extra_args: Sequence[Tuple[str, Any] | List[Any]] | None = ...,
     description: str = ...,
 ) -> None: ...
 def unregister_archive_format(name: str) -> None: ...
diff --git a/stdlib/@python2/site.pyi b/stdlib/@python2/site.pyi
index db7bbefcc794..c77c9397f612 100644
--- a/stdlib/@python2/site.pyi
+++ b/stdlib/@python2/site.pyi
@@ -1,12 +1,12 @@
-from typing import Iterable, List, Optional
+from typing import Iterable, List
 
 PREFIXES: List[str]
-ENABLE_USER_SITE: Optional[bool]
-USER_SITE: Optional[str]
-USER_BASE: Optional[str]
+ENABLE_USER_SITE: bool | None
+USER_SITE: str | None
+USER_BASE: str | None
 
 def main() -> None: ...
-def addsitedir(sitedir: str, known_paths: Optional[Iterable[str]] = ...) -> None: ...
-def getsitepackages(prefixes: Optional[Iterable[str]] = ...) -> List[str]: ...
+def addsitedir(sitedir: str, known_paths: Iterable[str] | None = ...) -> None: ...
+def getsitepackages(prefixes: Iterable[str] | None = ...) -> List[str]: ...
 def getuserbase() -> str: ...
 def getusersitepackages() -> str: ...
diff --git a/stdlib/@python2/smtpd.pyi b/stdlib/@python2/smtpd.pyi
index 33d84ffde4c8..1c17b82d8ab5 100644
--- a/stdlib/@python2/smtpd.pyi
+++ b/stdlib/@python2/smtpd.pyi
@@ -1,7 +1,7 @@
 import asynchat
 import asyncore
 import socket
-from typing import Any, List, Optional, Text, Tuple, Type, Union
+from typing import Any, List, Text, Tuple, Type
 
 _Address = Tuple[str, int]  # (host, port)
 
@@ -29,17 +29,17 @@ class SMTPServer(asyncore.dispatcher):
     def __init__(self, localaddr: _Address, remoteaddr: _Address, data_size_limit: int = ...) -> None: ...
     def handle_accepted(self, conn: socket.socket, addr: Any) -> None: ...
     def process_message(
-        self, peer: _Address, mailfrom: str, rcpttos: List[Text], data: Union[bytes, str], **kwargs: Any
-    ) -> Optional[str]: ...
+        self, peer: _Address, mailfrom: str, rcpttos: List[Text], data: bytes | str, **kwargs: Any
+    ) -> str | None: ...
 
 class DebuggingServer(SMTPServer): ...
 
 class PureProxy(SMTPServer):
     def process_message(  # type: ignore
-        self, peer: _Address, mailfrom: str, rcpttos: List[Text], data: Union[bytes, str]
-    ) -> Optional[str]: ...
+        self, peer: _Address, mailfrom: str, rcpttos: List[Text], data: bytes | str
+    ) -> str | None: ...
 
 class MailmanProxy(PureProxy):
     def process_message(  # type: ignore
-        self, peer: _Address, mailfrom: str, rcpttos: List[Text], data: Union[bytes, str]
-    ) -> Optional[str]: ...
+        self, peer: _Address, mailfrom: str, rcpttos: List[Text], data: bytes | str
+    ) -> str | None: ...
diff --git a/stdlib/@python2/sndhdr.pyi b/stdlib/@python2/sndhdr.pyi
index a5ae485c24a2..189529fd21d6 100644
--- a/stdlib/@python2/sndhdr.pyi
+++ b/stdlib/@python2/sndhdr.pyi
@@ -1,6 +1,6 @@
-from typing import Optional, Text, Tuple, Union
+from typing import Text, Tuple, Union
 
 _SndHeaders = Tuple[str, int, int, int, Union[int, str]]
 
-def what(filename: Text) -> Optional[_SndHeaders]: ...
-def whathdr(filename: Text) -> Optional[_SndHeaders]: ...
+def what(filename: Text) -> _SndHeaders | None: ...
+def whathdr(filename: Text) -> _SndHeaders | None: ...
diff --git a/stdlib/@python2/socket.pyi b/stdlib/@python2/socket.pyi
index ea3d47757a77..2bf719dd9faa 100644
--- a/stdlib/@python2/socket.pyi
+++ b/stdlib/@python2/socket.pyi
@@ -1,5 +1,5 @@
 import sys
-from typing import Any, BinaryIO, Iterable, List, Optional, Text, Tuple, TypeVar, Union, overload
+from typing import Any, BinaryIO, Iterable, List, Text, Tuple, TypeVar, Union, overload
 
 # ----- Constants -----
 # Some socket families are listed in the "Socket families" section of the docs,
@@ -389,10 +389,10 @@ class socket:
     def __init__(self, family: int = ..., type: int = ..., proto: int = ...) -> None: ...
     # --- methods ---
     def accept(self) -> Tuple[socket, _RetAddress]: ...
-    def bind(self, address: Union[_Address, bytes]) -> None: ...
+    def bind(self, address: _Address | bytes) -> None: ...
     def close(self) -> None: ...
-    def connect(self, address: Union[_Address, bytes]) -> None: ...
-    def connect_ex(self, address: Union[_Address, bytes]) -> int: ...
+    def connect(self, address: _Address | bytes) -> None: ...
+    def connect_ex(self, address: _Address | bytes) -> int: ...
     def detach(self) -> int: ...
     def dup(self) -> socket: ...
     def fileno(self) -> int: ...
@@ -402,9 +402,9 @@ class socket:
     def getsockopt(self, level: int, optname: int) -> int: ...
     @overload
     def getsockopt(self, level: int, optname: int, buflen: int) -> bytes: ...
-    def gettimeout(self) -> Optional[float]: ...
+    def gettimeout(self) -> float | None: ...
     if sys.platform == "win32":
-        def ioctl(self, control: int, option: Union[int, Tuple[int, int, int]]) -> None: ...
+        def ioctl(self, control: int, option: int | Tuple[int, int, int]) -> None: ...
     def listen(self, __backlog: int) -> None: ...
     # Note that the makefile's documented windows-specific behavior is not represented
     def makefile(self, mode: unicode = ..., buffering: int = ...) -> BinaryIO: ...
@@ -419,8 +419,8 @@ class socket:
     @overload
     def sendto(self, data: bytes, flags: int, address: _Address) -> int: ...
     def setblocking(self, flag: bool) -> None: ...
-    def settimeout(self, value: Optional[float]) -> None: ...
-    def setsockopt(self, level: int, optname: int, value: Union[int, bytes]) -> None: ...
+    def settimeout(self, value: float | None) -> None: ...
+    def setsockopt(self, level: int, optname: int, value: int | bytes) -> None: ...
     if sys.platform == "win32":
         def share(self, process_id: int) -> bytes: ...
     def shutdown(self, how: int) -> None: ...
@@ -428,16 +428,16 @@ class socket:
 # ----- Functions -----
 
 def create_connection(
-    address: Tuple[Optional[str], int],
-    timeout: Optional[float] = ...,
-    source_address: Optional[Tuple[Union[bytearray, bytes, Text], int]] = ...,
+    address: Tuple[str | None, int],
+    timeout: float | None = ...,
+    source_address: Tuple[bytearray | bytes | Text, int] | None = ...,
 ) -> socket: ...
 def fromfd(fd: int, family: int, type: int, proto: int = ...) -> socket: ...
 
 # the 5th tuple item is an address
 def getaddrinfo(
-    host: Optional[Union[bytearray, bytes, Text]],
-    port: Union[str, int, None],
+    host: bytearray | bytes | Text | None,
+    port: str | int | None,
     family: int = ...,
     socktype: int = ...,
     proto: int = ...,
@@ -448,7 +448,7 @@ def gethostbyname(hostname: str) -> str: ...
 def gethostbyname_ex(hostname: str) -> Tuple[str, List[str], List[str]]: ...
 def gethostname() -> str: ...
 def gethostbyaddr(ip_address: str) -> Tuple[str, List[str], List[str]]: ...
-def getnameinfo(sockaddr: Union[Tuple[str, int], Tuple[str, int, int, int]], flags: int) -> Tuple[str, str]: ...
+def getnameinfo(sockaddr: Tuple[str, int] | Tuple[str, int, int, int], flags: int) -> Tuple[str, str]: ...
 def getprotobyname(protocolname: str) -> int: ...
 def getservbyname(servicename: str, protocolname: str = ...) -> int: ...
 def getservbyport(port: int, protocolname: str = ...) -> str: ...
@@ -457,7 +457,7 @@ if sys.platform == "win32":
     def socketpair(family: int = ..., type: int = ..., proto: int = ...) -> Tuple[socket, socket]: ...
 
 else:
-    def socketpair(family: Optional[int] = ..., type: int = ..., proto: int = ...) -> Tuple[socket, socket]: ...
+    def socketpair(family: int | None = ..., type: int = ..., proto: int = ...) -> Tuple[socket, socket]: ...
 
 def ntohl(x: int) -> int: ...  # param & ret val are 32-bit ints
 def ntohs(x: int) -> int: ...  # param & ret val are 16-bit ints
@@ -467,5 +467,5 @@ def inet_aton(ip_string: str) -> bytes: ...  # ret val 4 bytes in length
 def inet_ntoa(packed_ip: bytes) -> str: ...
 def inet_pton(address_family: int, ip_string: str) -> bytes: ...
 def inet_ntop(address_family: int, packed_ip: bytes) -> str: ...
-def getdefaulttimeout() -> Optional[float]: ...
-def setdefaulttimeout(timeout: Optional[float]) -> None: ...
+def getdefaulttimeout() -> float | None: ...
+def setdefaulttimeout(timeout: float | None) -> None: ...
diff --git a/stdlib/@python2/sqlite3/dbapi2.pyi b/stdlib/@python2/sqlite3/dbapi2.pyi
index e89ae080aed0..fadfcc8f5884 100644
--- a/stdlib/@python2/sqlite3/dbapi2.pyi
+++ b/stdlib/@python2/sqlite3/dbapi2.pyi
@@ -1,5 +1,5 @@
 from datetime import date, datetime, time
-from typing import Any, Callable, Generator, Iterable, Iterator, List, Optional, Protocol, Text, Tuple, Type, TypeVar, Union
+from typing import Any, Callable, Generator, Iterable, Iterator, List, Protocol, Text, Tuple, Type, TypeVar
 
 _T = TypeVar("_T")
 
@@ -62,17 +62,17 @@ version: str
 def adapt(obj, protocol, alternate): ...
 def complete_statement(sql: str) -> bool: ...
 def connect(
-    database: Union[bytes, Text],
+    database: bytes | Text,
     timeout: float = ...,
     detect_types: int = ...,
-    isolation_level: Optional[str] = ...,
+    isolation_level: str | None = ...,
     check_same_thread: bool = ...,
-    factory: Optional[Type[Connection]] = ...,
+    factory: Type[Connection] | None = ...,
     cached_statements: int = ...,
 ) -> Connection: ...
 def enable_callback_tracebacks(__enable: bool) -> None: ...
 def enable_shared_cache(enable: int) -> None: ...
-def register_adapter(__type: Type[_T], __caster: Callable[[_T], Union[int, float, str, bytes]]) -> None: ...
+def register_adapter(__type: Type[_T], __caster: Callable[[_T], int | float | str | bytes]) -> None: ...
 def register_converter(__name: str, __converter: Callable[[bytes], Any]) -> None: ...
 
 class Cache(object):
@@ -106,11 +106,11 @@ class Connection(object):
     def create_aggregate(self, name: str, n_arg: int, aggregate_class: Callable[[], _AggregateProtocol]) -> None: ...
     def create_collation(self, __name: str, __callback: Any) -> None: ...
     def create_function(self, name: str, num_params: int, func: Any) -> None: ...
-    def cursor(self, cursorClass: Optional[type] = ...) -> Cursor: ...
+    def cursor(self, cursorClass: type | None = ...) -> Cursor: ...
     def execute(self, sql: str, parameters: Iterable[Any] = ...) -> Cursor: ...
     # TODO: please check in executemany() if seq_of_parameters type is possible like this
     def executemany(self, __sql: str, __parameters: Iterable[Iterable[Any]]) -> Cursor: ...
-    def executescript(self, __sql_script: Union[bytes, Text]) -> Cursor: ...
+    def executescript(self, __sql_script: bytes | Text) -> Cursor: ...
     def interrupt(self, *args: Any, **kwargs: Any) -> None: ...
     def iterdump(self, *args: Any, **kwargs: Any) -> Generator[str, None, None]: ...
     def rollback(self, *args: Any, **kwargs: Any) -> None: ...
@@ -127,7 +127,7 @@ class Connection(object):
     def load_extension(self, path: str) -> None: ...
     def __call__(self, *args: Any, **kwargs: Any) -> Any: ...
     def __enter__(self) -> Connection: ...
-    def __exit__(self, t: Optional[type], exc: Optional[BaseException], tb: Optional[Any]) -> None: ...
+    def __exit__(self, t: type | None, exc: BaseException | None, tb: Any | None) -> None: ...
 
 class Cursor(Iterator[Any]):
     arraysize: Any
@@ -143,9 +143,9 @@ class Cursor(Iterator[Any]):
     def close(self, *args: Any, **kwargs: Any) -> None: ...
     def execute(self, __sql: str, __parameters: Iterable[Any] = ...) -> Cursor: ...
     def executemany(self, __sql: str, __seq_of_parameters: Iterable[Iterable[Any]]) -> Cursor: ...
-    def executescript(self, __sql_script: Union[bytes, Text]) -> Cursor: ...
+    def executescript(self, __sql_script: bytes | Text) -> Cursor: ...
     def fetchall(self) -> List[Any]: ...
-    def fetchmany(self, size: Optional[int] = ...) -> List[Any]: ...
+    def fetchmany(self, size: int | None = ...) -> List[Any]: ...
     def fetchone(self) -> Any: ...
     def setinputsizes(self, *args: Any, **kwargs: Any) -> None: ...
     def setoutputsize(self, *args: Any, **kwargs: Any) -> None: ...
diff --git a/stdlib/@python2/sre_compile.pyi b/stdlib/@python2/sre_compile.pyi
index 23317a918dad..efc3e568a07c 100644
--- a/stdlib/@python2/sre_compile.pyi
+++ b/stdlib/@python2/sre_compile.pyi
@@ -12,11 +12,11 @@ from sre_constants import (
     SRE_INFO_PREFIX as SRE_INFO_PREFIX,
 )
 from sre_parse import SubPattern
-from typing import Any, List, Pattern, Tuple, Type, Union
+from typing import Any, List, Pattern, Tuple, Type
 
 MAXCODE: int
 STRING_TYPES: Tuple[Type[str], Type[unicode]]
 _IsStringType = int
 
 def isstring(obj: Any) -> _IsStringType: ...
-def compile(p: Union[str, bytes, SubPattern], flags: int = ...) -> Pattern[Any]: ...
+def compile(p: str | bytes | SubPattern, flags: int = ...) -> Pattern[Any]: ...
diff --git a/stdlib/@python2/sre_parse.pyi b/stdlib/@python2/sre_parse.pyi
index e2a0be4e3bf1..35f6d4d32ae2 100644
--- a/stdlib/@python2/sre_parse.pyi
+++ b/stdlib/@python2/sre_parse.pyi
@@ -7,7 +7,7 @@ OCTDIGITS: Set[Any]
 HEXDIGITS: Set[Any]
 WHITESPACE: Set[Any]
 ESCAPES: Dict[str, Tuple[str, int]]
-CATEGORIES: Dict[str, Union[Tuple[str, str], Tuple[str, List[Tuple[str, str]]]]]
+CATEGORIES: Dict[str, Tuple[str, str] | Tuple[str, List[Tuple[str, str]]]]
 FLAGS: Dict[str, int]
 
 class Pattern:
@@ -31,13 +31,13 @@ _CodeType = Union[str, _AvType]
 class SubPattern:
     pattern: str
     data: List[_CodeType]
-    width: Optional[int]
+    width: int | None
     def __init__(self, pattern, data: List[_CodeType] = ...) -> None: ...
     def dump(self, level: int = ...) -> None: ...
     def __len__(self) -> int: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
-    def __getitem__(self, index: Union[int, slice]) -> Union[SubPattern, _CodeType]: ...
-    def __setitem__(self, index: Union[int, slice], code: _CodeType): ...
+    def __delitem__(self, index: int | slice) -> None: ...
+    def __getitem__(self, index: int | slice) -> SubPattern | _CodeType: ...
+    def __setitem__(self, index: int | slice, code: _CodeType): ...
     def insert(self, index, code: _CodeType) -> None: ...
     def append(self, code: _CodeType) -> None: ...
     def getwidth(self) -> int: ...
@@ -47,8 +47,8 @@ class Tokenizer:
     index: int
     def __init__(self, string: str) -> None: ...
     def match(self, char: str, skip: int = ...) -> int: ...
-    def get(self) -> Optional[str]: ...
-    def tell(self) -> Tuple[int, Optional[str]]: ...
+    def get(self) -> str | None: ...
+    def tell(self) -> Tuple[int, str | None]: ...
     def seek(self, index: int) -> None: ...
 
 def isident(char: str) -> bool: ...
diff --git a/stdlib/@python2/ssl.pyi b/stdlib/@python2/ssl.pyi
index b9693fa89768..aabecaaba87a 100644
--- a/stdlib/@python2/ssl.pyi
+++ b/stdlib/@python2/ssl.pyi
@@ -27,30 +27,30 @@ class CertificateError(ValueError): ...
 
 def wrap_socket(
     sock: socket.socket,
-    keyfile: Optional[str] = ...,
-    certfile: Optional[str] = ...,
+    keyfile: str | None = ...,
+    certfile: str | None = ...,
     server_side: bool = ...,
     cert_reqs: int = ...,
     ssl_version: int = ...,
-    ca_certs: Optional[str] = ...,
+    ca_certs: str | None = ...,
     do_handshake_on_connect: bool = ...,
     suppress_ragged_eofs: bool = ...,
-    ciphers: Optional[str] = ...,
+    ciphers: str | None = ...,
 ) -> SSLSocket: ...
 def create_default_context(
-    purpose: Any = ..., *, cafile: Optional[str] = ..., capath: Optional[str] = ..., cadata: Union[Text, bytes, None] = ...
+    purpose: Any = ..., *, cafile: str | None = ..., capath: str | None = ..., cadata: Text | bytes | None = ...
 ) -> SSLContext: ...
 def _create_unverified_context(
     protocol: int = ...,
     *,
-    cert_reqs: Optional[int] = ...,
+    cert_reqs: int | None = ...,
     check_hostname: bool = ...,
     purpose: Any = ...,
-    certfile: Optional[str] = ...,
-    keyfile: Optional[str] = ...,
-    cafile: Optional[str] = ...,
-    capath: Optional[str] = ...,
-    cadata: Union[Text, bytes, None] = ...,
+    certfile: str | None = ...,
+    keyfile: str | None = ...,
+    cafile: str | None = ...,
+    capath: str | None = ...,
+    cadata: Text | bytes | None = ...,
 ) -> SSLContext: ...
 
 _create_default_https_context: Callable[..., SSLContext]
@@ -60,7 +60,7 @@ def RAND_egd(path: str) -> None: ...
 def RAND_add(__s: bytes, __entropy: float) -> None: ...
 def match_hostname(cert: _PeerCertRetType, hostname: str) -> None: ...
 def cert_time_to_seconds(cert_time: str) -> int: ...
-def get_server_certificate(addr: Tuple[str, int], ssl_version: int = ..., ca_certs: Optional[str] = ...) -> str: ...
+def get_server_certificate(addr: Tuple[str, int], ssl_version: int = ..., ca_certs: str | None = ...) -> str: ...
 def DER_cert_to_PEM_cert(der_cert_bytes: bytes) -> str: ...
 def PEM_cert_to_DER_cert(pem_cert_string: str) -> bytes: ...
 
@@ -157,57 +157,57 @@ class Purpose(_ASN1Object):
 class SSLSocket(socket.socket):
     context: SSLContext
     server_side: bool
-    server_hostname: Optional[str]
+    server_hostname: str | None
     def __init__(
         self,
-        sock: Optional[socket.socket] = ...,
-        keyfile: Optional[str] = ...,
-        certfile: Optional[str] = ...,
+        sock: socket.socket | None = ...,
+        keyfile: str | None = ...,
+        certfile: str | None = ...,
         server_side: bool = ...,
         cert_reqs: int = ...,
         ssl_version: int = ...,
-        ca_certs: Optional[str] = ...,
+        ca_certs: str | None = ...,
         do_handshake_on_connect: bool = ...,
         family: int = ...,
         type: int = ...,
         proto: int = ...,
-        fileno: Optional[int] = ...,
+        fileno: int | None = ...,
         suppress_ragged_eofs: bool = ...,
-        npn_protocols: Optional[Iterable[str]] = ...,
-        ciphers: Optional[str] = ...,
-        server_hostname: Optional[str] = ...,
-        _context: Optional[SSLContext] = ...,
-        _session: Optional[Any] = ...,
+        npn_protocols: Iterable[str] | None = ...,
+        ciphers: str | None = ...,
+        server_hostname: str | None = ...,
+        _context: SSLContext | None = ...,
+        _session: Any | None = ...,
     ) -> None: ...
-    def connect(self, addr: Union[socket._Address, bytes]) -> None: ...
-    def connect_ex(self, addr: Union[socket._Address, bytes]) -> int: ...
+    def connect(self, addr: socket._Address | bytes) -> None: ...
+    def connect_ex(self, addr: socket._Address | bytes) -> int: ...
     def recv(self, buflen: int = ..., flags: int = ...) -> bytes: ...
-    def recv_into(self, buffer: socket._WriteBuffer, nbytes: Optional[int] = ..., flags: int = ...) -> int: ...
+    def recv_into(self, buffer: socket._WriteBuffer, nbytes: int | None = ..., flags: int = ...) -> int: ...
     def recvfrom(self, buflen: int = ..., flags: int = ...) -> tuple[bytes, socket._RetAddress]: ...
     def recvfrom_into(
-        self, buffer: socket._WriteBuffer, nbytes: Optional[int] = ..., flags: int = ...
+        self, buffer: socket._WriteBuffer, nbytes: int | None = ..., flags: int = ...
     ) -> tuple[int, socket._RetAddress]: ...
     @overload
     def sendto(self, data: bytes, flags_or_addr: socket._Address) -> int: ...
     @overload
-    def sendto(self, data: bytes, flags_or_addr: Union[int, socket._Address], addr: Optional[socket._Address] = ...) -> int: ...
-    def read(self, len: int = ..., buffer: Optional[bytearray] = ...) -> bytes: ...
+    def sendto(self, data: bytes, flags_or_addr: int | socket._Address, addr: socket._Address | None = ...) -> int: ...
+    def read(self, len: int = ..., buffer: bytearray | None = ...) -> bytes: ...
     def write(self, data: bytes) -> int: ...
     def do_handshake(self, block: bool = ...) -> None: ...  # block is undocumented
     @overload
-    def getpeercert(self, binary_form: Literal[False] = ...) -> Optional[_PeerCertRetDictType]: ...
+    def getpeercert(self, binary_form: Literal[False] = ...) -> _PeerCertRetDictType | None: ...
     @overload
-    def getpeercert(self, binary_form: Literal[True]) -> Optional[bytes]: ...
+    def getpeercert(self, binary_form: Literal[True]) -> bytes | None: ...
     @overload
     def getpeercert(self, binary_form: bool) -> _PeerCertRetType: ...
-    def cipher(self) -> Optional[Tuple[str, str, int]]: ...
-    def compression(self) -> Optional[str]: ...
-    def get_channel_binding(self, cb_type: str = ...) -> Optional[bytes]: ...
-    def selected_alpn_protocol(self) -> Optional[str]: ...
-    def selected_npn_protocol(self) -> Optional[str]: ...
+    def cipher(self) -> Tuple[str, str, int] | None: ...
+    def compression(self) -> str | None: ...
+    def get_channel_binding(self, cb_type: str = ...) -> bytes | None: ...
+    def selected_alpn_protocol(self) -> str | None: ...
+    def selected_npn_protocol(self) -> str | None: ...
     def accept(self) -> Tuple[SSLSocket, socket._RetAddress]: ...
     def unwrap(self) -> socket.socket: ...
-    def version(self) -> Optional[str]: ...
+    def version(self) -> str | None: ...
     def pending(self) -> int: ...
 
 class SSLContext:
@@ -220,19 +220,17 @@ class SSLContext:
     verify_mode: int
     def __init__(self, protocol: int) -> None: ...
     def cert_store_stats(self) -> Dict[str, int]: ...
-    def load_cert_chain(
-        self, certfile: StrPath, keyfile: Optional[StrPath] = ..., password: Optional[_PasswordType] = ...
-    ) -> None: ...
+    def load_cert_chain(self, certfile: StrPath, keyfile: StrPath | None = ..., password: _PasswordType | None = ...) -> None: ...
     def load_default_certs(self, purpose: Purpose = ...) -> None: ...
     def load_verify_locations(
-        self, cafile: Optional[StrPath] = ..., capath: Optional[StrPath] = ..., cadata: Union[Text, bytes, None] = ...
+        self, cafile: StrPath | None = ..., capath: StrPath | None = ..., cadata: Text | bytes | None = ...
     ) -> None: ...
-    def get_ca_certs(self, binary_form: bool = ...) -> Union[List[_PeerCertRetDictType], List[bytes]]: ...
+    def get_ca_certs(self, binary_form: bool = ...) -> List[_PeerCertRetDictType] | List[bytes]: ...
     def set_default_verify_paths(self) -> None: ...
     def set_ciphers(self, __cipherlist: str) -> None: ...
     def set_alpn_protocols(self, alpn_protocols: Iterable[str]) -> None: ...
     def set_npn_protocols(self, npn_protocols: Iterable[str]) -> None: ...
-    def set_servername_callback(self, __method: Optional[_SrvnmeCbType]) -> None: ...
+    def set_servername_callback(self, __method: _SrvnmeCbType | None) -> None: ...
     def load_dh_params(self, __path: str) -> None: ...
     def set_ecdh_curve(self, __name: str) -> None: ...
     def wrap_socket(
@@ -241,7 +239,7 @@ class SSLContext:
         server_side: bool = ...,
         do_handshake_on_connect: bool = ...,
         suppress_ragged_eofs: bool = ...,
-        server_hostname: Optional[str] = ...,
+        server_hostname: str | None = ...,
     ) -> SSLSocket: ...
     def session_stats(self) -> Dict[str, int]: ...
 
diff --git a/stdlib/@python2/string.pyi b/stdlib/@python2/string.pyi
index a2b0a9d25ddb..fe028dab39bd 100644
--- a/stdlib/@python2/string.pyi
+++ b/stdlib/@python2/string.pyi
@@ -1,4 +1,4 @@
-from typing import Any, AnyStr, Iterable, List, Mapping, Sequence, Text, Tuple, Union, overload
+from typing import Any, AnyStr, Iterable, List, Mapping, Sequence, Text, Tuple, overload
 
 ascii_letters: str
 ascii_lowercase: str
@@ -48,13 +48,13 @@ class Template:
     template: Text
     def __init__(self, template: Text) -> None: ...
     @overload
-    def substitute(self, mapping: Union[Mapping[str, str], Mapping[unicode, str]] = ..., **kwds: str) -> str: ...
+    def substitute(self, mapping: Mapping[str, str] | Mapping[unicode, str] = ..., **kwds: str) -> str: ...
     @overload
-    def substitute(self, mapping: Union[Mapping[str, Text], Mapping[unicode, Text]] = ..., **kwds: Text) -> Text: ...
+    def substitute(self, mapping: Mapping[str, Text] | Mapping[unicode, Text] = ..., **kwds: Text) -> Text: ...
     @overload
-    def safe_substitute(self, mapping: Union[Mapping[str, str], Mapping[unicode, str]] = ..., **kwds: str) -> str: ...
+    def safe_substitute(self, mapping: Mapping[str, str] | Mapping[unicode, str] = ..., **kwds: str) -> str: ...
     @overload
-    def safe_substitute(self, mapping: Union[Mapping[str, Text], Mapping[unicode, Text]], **kwds: Text) -> Text: ...
+    def safe_substitute(self, mapping: Mapping[str, Text] | Mapping[unicode, Text], **kwds: Text) -> Text: ...
 
 # TODO(MichalPokorny): This is probably badly and/or loosely typed.
 class Formatter(object):
@@ -62,7 +62,7 @@ class Formatter(object):
     def vformat(self, format_string: str, args: Sequence[Any], kwargs: Mapping[str, Any]) -> str: ...
     def parse(self, format_string: str) -> Iterable[Tuple[str, str, str, str]]: ...
     def get_field(self, field_name: str, args: Sequence[Any], kwargs: Mapping[str, Any]) -> Any: ...
-    def get_value(self, key: Union[int, str], args: Sequence[Any], kwargs: Mapping[str, Any]) -> Any: ...
-    def check_unused_args(self, used_args: Sequence[Union[int, str]], args: Sequence[Any], kwargs: Mapping[str, Any]) -> None: ...
+    def get_value(self, key: int | str, args: Sequence[Any], kwargs: Mapping[str, Any]) -> Any: ...
+    def check_unused_args(self, used_args: Sequence[int | str], args: Sequence[Any], kwargs: Mapping[str, Any]) -> None: ...
     def format_field(self, value: Any, format_spec: str) -> Any: ...
     def convert_field(self, value: Any, conversion: str) -> Any: ...
diff --git a/stdlib/@python2/stringold.pyi b/stdlib/@python2/stringold.pyi
index 271da8357c70..d221547f1c07 100644
--- a/stdlib/@python2/stringold.pyi
+++ b/stdlib/@python2/stringold.pyi
@@ -1,4 +1,4 @@
-from typing import AnyStr, Iterable, List, Optional
+from typing import AnyStr, Iterable, List
 
 whitespace: str
 lowercase: str
@@ -8,7 +8,7 @@ digits: str
 hexdigits: str
 octdigits: str
 _idmap: str
-_idmapL: Optional[List[str]]
+_idmapL: List[str] | None
 index_error = ValueError
 atoi_error = ValueError
 atof_error = ValueError
diff --git a/stdlib/@python2/subprocess.pyi b/stdlib/@python2/subprocess.pyi
index 28a4c0574419..8c101272322a 100644
--- a/stdlib/@python2/subprocess.pyi
+++ b/stdlib/@python2/subprocess.pyi
@@ -16,8 +16,8 @@ def call(
     preexec_fn: Callable[[], Any] = ...,
     close_fds: bool = ...,
     shell: bool = ...,
-    cwd: Optional[_TXT] = ...,
-    env: Optional[_ENV] = ...,
+    cwd: _TXT | None = ...,
+    env: _ENV | None = ...,
     universal_newlines: bool = ...,
     startupinfo: Any = ...,
     creationflags: int = ...,
@@ -32,8 +32,8 @@ def check_call(
     preexec_fn: Callable[[], Any] = ...,
     close_fds: bool = ...,
     shell: bool = ...,
-    cwd: Optional[_TXT] = ...,
-    env: Optional[_ENV] = ...,
+    cwd: _TXT | None = ...,
+    env: _ENV | None = ...,
     universal_newlines: bool = ...,
     startupinfo: Any = ...,
     creationflags: int = ...,
@@ -49,8 +49,8 @@ def check_output(
     preexec_fn: Callable[[], Any] = ...,
     close_fds: bool = ...,
     shell: bool = ...,
-    cwd: Optional[_TXT] = ...,
-    env: Optional[_ENV] = ...,
+    cwd: _TXT | None = ...,
+    env: _ENV | None = ...,
     universal_newlines: bool = ...,
     startupinfo: Any = ...,
     creationflags: int = ...,
@@ -65,38 +65,38 @@ class CalledProcessError(Exception):
     cmd: Any
     # morally: Optional[bytes]
     output: bytes
-    def __init__(self, returncode: int, cmd: _CMD, output: Optional[bytes] = ...) -> None: ...
+    def __init__(self, returncode: int, cmd: _CMD, output: bytes | None = ...) -> None: ...
 
 # We use a dummy type variable used to make Popen generic like it is in python 3
 _T = TypeVar("_T", bound=bytes)
 
 class Popen(Generic[_T]):
-    stdin: Optional[IO[bytes]]
-    stdout: Optional[IO[bytes]]
-    stderr: Optional[IO[bytes]]
+    stdin: IO[bytes] | None
+    stdout: IO[bytes] | None
+    stderr: IO[bytes] | None
     pid: int
     returncode: int
     def __new__(
         cls,
         args: _CMD,
         bufsize: int = ...,
-        executable: Optional[_TXT] = ...,
-        stdin: Optional[_FILE] = ...,
-        stdout: Optional[_FILE] = ...,
-        stderr: Optional[_FILE] = ...,
-        preexec_fn: Optional[Callable[[], Any]] = ...,
+        executable: _TXT | None = ...,
+        stdin: _FILE | None = ...,
+        stdout: _FILE | None = ...,
+        stderr: _FILE | None = ...,
+        preexec_fn: Callable[[], Any] | None = ...,
         close_fds: bool = ...,
         shell: bool = ...,
-        cwd: Optional[_TXT] = ...,
-        env: Optional[_ENV] = ...,
+        cwd: _TXT | None = ...,
+        env: _ENV | None = ...,
         universal_newlines: bool = ...,
-        startupinfo: Optional[Any] = ...,
+        startupinfo: Any | None = ...,
         creationflags: int = ...,
     ) -> Popen[bytes]: ...
-    def poll(self) -> Optional[int]: ...
+    def poll(self) -> int | None: ...
     def wait(self) -> int: ...
     # morally: -> Tuple[Optional[bytes], Optional[bytes]]
-    def communicate(self, input: Optional[_TXT] = ...) -> Tuple[bytes, bytes]: ...
+    def communicate(self, input: _TXT | None = ...) -> Tuple[bytes, bytes]: ...
     def send_signal(self, signal: int) -> None: ...
     def terminate(self) -> None: ...
     def kill(self) -> None: ...
diff --git a/stdlib/@python2/sunau.pyi b/stdlib/@python2/sunau.pyi
index e40ae2181be0..3ee4b9651346 100644
--- a/stdlib/@python2/sunau.pyi
+++ b/stdlib/@python2/sunau.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, NoReturn, Optional, Text, Tuple, Union
+from typing import IO, Any, NoReturn, Text, Tuple, Union
 
 _File = Union[Text, IO[bytes]]
 
@@ -23,7 +23,7 @@ _sunau_params = Tuple[int, int, int, int, str, str]
 
 class Au_read:
     def __init__(self, f: _File) -> None: ...
-    def getfp(self) -> Optional[IO[bytes]]: ...
+    def getfp(self) -> IO[bytes] | None: ...
     def rewind(self) -> None: ...
     def close(self) -> None: ...
     def tell(self) -> int: ...
@@ -37,7 +37,7 @@ class Au_read:
     def getmarkers(self) -> None: ...
     def getmark(self, id: Any) -> NoReturn: ...
     def setpos(self, pos: int) -> None: ...
-    def readframes(self, nframes: int) -> Optional[bytes]: ...
+    def readframes(self, nframes: int) -> bytes | None: ...
 
 class Au_write:
     def __init__(self, f: _File) -> None: ...
@@ -61,6 +61,6 @@ class Au_write:
     def close(self) -> None: ...
 
 # Returns a Au_read if mode is rb and Au_write if mode is wb
-def open(f: _File, mode: Optional[str] = ...) -> Any: ...
+def open(f: _File, mode: str | None = ...) -> Any: ...
 
 openfp = open
diff --git a/stdlib/@python2/symtable.pyi b/stdlib/@python2/symtable.pyi
index c7b8092aedbb..bd3f25c7cb63 100644
--- a/stdlib/@python2/symtable.pyi
+++ b/stdlib/@python2/symtable.pyi
@@ -1,4 +1,4 @@
-from typing import Any, List, Optional, Sequence, Text, Tuple
+from typing import Any, List, Sequence, Text, Tuple
 
 def symtable(code: Text, filename: Text, compile_type: Text) -> SymbolTable: ...
 
@@ -28,7 +28,7 @@ class Class(SymbolTable):
     def get_methods(self) -> Tuple[str, ...]: ...
 
 class Symbol(object):
-    def __init__(self, name: str, flags: int, namespaces: Optional[Sequence[SymbolTable]] = ...) -> None: ...
+    def __init__(self, name: str, flags: int, namespaces: Sequence[SymbolTable] | None = ...) -> None: ...
     def get_name(self) -> str: ...
     def is_referenced(self) -> bool: ...
     def is_parameter(self) -> bool: ...
diff --git a/stdlib/@python2/sys.pyi b/stdlib/@python2/sys.pyi
index 7852911b6532..d4858ec251fa 100644
--- a/stdlib/@python2/sys.pyi
+++ b/stdlib/@python2/sys.pyi
@@ -1,5 +1,5 @@
 from types import ClassType, FrameType, TracebackType
-from typing import IO, Any, Callable, Dict, List, NoReturn, Optional, Text, Tuple, Type, Union
+from typing import IO, Any, Callable, Dict, List, NoReturn, Text, Tuple, Type, Union
 
 # The following type alias are stub-only and do not exist during runtime
 _ExcInfo = Tuple[Type[BaseException], BaseException, TracebackType]
@@ -86,8 +86,8 @@ path_hooks: List[Any]
 path_importer_cache: Dict[str, Any]
 displayhook: Callable[[object], Any]
 excepthook: Callable[[Type[BaseException], BaseException, TracebackType], Any]
-exc_type: Optional[type]
-exc_value: Union[BaseException, ClassType]
+exc_type: type | None
+exc_value: BaseException | ClassType
 exc_traceback: TracebackType
 
 class _WindowsVersionType:
@@ -120,8 +120,8 @@ def getfilesystemencoding() -> str: ...  # In practice, never returns None
 def getrefcount(arg: Any) -> int: ...
 def getrecursionlimit() -> int: ...
 def getsizeof(obj: object, default: int = ...) -> int: ...
-def getprofile() -> Optional[Any]: ...
-def gettrace() -> Optional[Any]: ...
+def getprofile() -> Any | None: ...
+def gettrace() -> Any | None: ...
 def setcheckinterval(interval: int) -> None: ...  # deprecated
 def setdlopenflags(n: int) -> None: ...
 def setdefaultencoding(encoding: Text) -> None: ...  # only exists after reload(sys)
diff --git a/stdlib/@python2/sysconfig.pyi b/stdlib/@python2/sysconfig.pyi
index c5f00ee9ea08..2bef9e467bc9 100644
--- a/stdlib/@python2/sysconfig.pyi
+++ b/stdlib/@python2/sysconfig.pyi
@@ -1,17 +1,17 @@
-from typing import IO, Any, Dict, List, Optional, Tuple, overload
+from typing import IO, Any, Dict, List, Tuple, overload
 
-def get_config_var(name: str) -> Optional[str]: ...
+def get_config_var(name: str) -> str | None: ...
 @overload
 def get_config_vars() -> Dict[str, Any]: ...
 @overload
 def get_config_vars(arg: str, *args: str) -> List[Any]: ...
 def get_scheme_names() -> Tuple[str, ...]: ...
 def get_path_names() -> Tuple[str, ...]: ...
-def get_path(name: str, scheme: str = ..., vars: Optional[Dict[str, Any]] = ..., expand: bool = ...) -> str: ...
-def get_paths(scheme: str = ..., vars: Optional[Dict[str, Any]] = ..., expand: bool = ...) -> Dict[str, str]: ...
+def get_path(name: str, scheme: str = ..., vars: Dict[str, Any] | None = ..., expand: bool = ...) -> str: ...
+def get_paths(scheme: str = ..., vars: Dict[str, Any] | None = ..., expand: bool = ...) -> Dict[str, str]: ...
 def get_python_version() -> str: ...
 def get_platform() -> str: ...
 def is_python_build(check_home: bool = ...) -> bool: ...
-def parse_config_h(fp: IO[Any], vars: Optional[Dict[str, Any]] = ...) -> Dict[str, Any]: ...
+def parse_config_h(fp: IO[Any], vars: Dict[str, Any] | None = ...) -> Dict[str, Any]: ...
 def get_config_h_filename() -> str: ...
 def get_makefile_filename() -> str: ...
diff --git a/stdlib/@python2/tarfile.pyi b/stdlib/@python2/tarfile.pyi
index 169d7d2c89f6..c08c96b6f0d5 100644
--- a/stdlib/@python2/tarfile.pyi
+++ b/stdlib/@python2/tarfile.pyi
@@ -1,6 +1,6 @@
 import io
 from types import TracebackType
-from typing import IO, Callable, Dict, Iterable, Iterator, List, Mapping, Optional, Text, Tuple, Type, Union
+from typing import IO, Callable, Dict, Iterable, Iterator, List, Mapping, Text, Tuple, Type
 
 # tar constants
 NUL: bytes
@@ -50,21 +50,21 @@ TAR_PLAIN: int
 TAR_GZIPPED: int
 
 def open(
-    name: Optional[Text] = ...,
+    name: Text | None = ...,
     mode: str = ...,
-    fileobj: Optional[IO[bytes]] = ...,
+    fileobj: IO[bytes] | None = ...,
     bufsize: int = ...,
     *,
-    format: Optional[int] = ...,
-    tarinfo: Optional[Type[TarInfo]] = ...,
-    dereference: Optional[bool] = ...,
-    ignore_zeros: Optional[bool] = ...,
-    encoding: Optional[str] = ...,
+    format: int | None = ...,
+    tarinfo: Type[TarInfo] | None = ...,
+    dereference: bool | None = ...,
+    ignore_zeros: bool | None = ...,
+    encoding: str | None = ...,
     errors: str = ...,
-    pax_headers: Optional[Mapping[str, str]] = ...,
-    debug: Optional[int] = ...,
-    errorlevel: Optional[int] = ...,
-    compresslevel: Optional[int] = ...,
+    pax_headers: Mapping[str, str] | None = ...,
+    debug: int | None = ...,
+    errorlevel: int | None = ...,
+    compresslevel: int | None = ...,
 ) -> TarFile: ...
 
 class ExFileObject(io.BufferedReader):
@@ -72,136 +72,136 @@ class ExFileObject(io.BufferedReader):
 
 class TarFile(Iterable[TarInfo]):
     OPEN_METH: Mapping[str, str]
-    name: Optional[Text]
+    name: Text | None
     mode: str
-    fileobj: Optional[IO[bytes]]
-    format: Optional[int]
+    fileobj: IO[bytes] | None
+    format: int | None
     tarinfo: Type[TarInfo]
-    dereference: Optional[bool]
-    ignore_zeros: Optional[bool]
-    encoding: Optional[str]
+    dereference: bool | None
+    ignore_zeros: bool | None
+    encoding: str | None
     errors: str
     fileobject: Type[ExFileObject]
-    pax_headers: Optional[Mapping[str, str]]
-    debug: Optional[int]
-    errorlevel: Optional[int]
+    pax_headers: Mapping[str, str] | None
+    debug: int | None
+    errorlevel: int | None
     offset: int  # undocumented
     posix: bool
     def __init__(
         self,
-        name: Optional[Text] = ...,
+        name: Text | None = ...,
         mode: str = ...,
-        fileobj: Optional[IO[bytes]] = ...,
-        format: Optional[int] = ...,
-        tarinfo: Optional[Type[TarInfo]] = ...,
-        dereference: Optional[bool] = ...,
-        ignore_zeros: Optional[bool] = ...,
-        encoding: Optional[str] = ...,
+        fileobj: IO[bytes] | None = ...,
+        format: int | None = ...,
+        tarinfo: Type[TarInfo] | None = ...,
+        dereference: bool | None = ...,
+        ignore_zeros: bool | None = ...,
+        encoding: str | None = ...,
         errors: str = ...,
-        pax_headers: Optional[Mapping[str, str]] = ...,
-        debug: Optional[int] = ...,
-        errorlevel: Optional[int] = ...,
-        copybufsize: Optional[int] = ...,  # undocumented
+        pax_headers: Mapping[str, str] | None = ...,
+        debug: int | None = ...,
+        errorlevel: int | None = ...,
+        copybufsize: int | None = ...,  # undocumented
     ) -> None: ...
     def __enter__(self) -> TarFile: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
     def __iter__(self) -> Iterator[TarInfo]: ...
     @classmethod
     def open(
         cls,
-        name: Optional[Text] = ...,
+        name: Text | None = ...,
         mode: str = ...,
-        fileobj: Optional[IO[bytes]] = ...,
+        fileobj: IO[bytes] | None = ...,
         bufsize: int = ...,
         *,
-        format: Optional[int] = ...,
-        tarinfo: Optional[Type[TarInfo]] = ...,
-        dereference: Optional[bool] = ...,
-        ignore_zeros: Optional[bool] = ...,
-        encoding: Optional[str] = ...,
+        format: int | None = ...,
+        tarinfo: Type[TarInfo] | None = ...,
+        dereference: bool | None = ...,
+        ignore_zeros: bool | None = ...,
+        encoding: str | None = ...,
         errors: str = ...,
-        pax_headers: Optional[Mapping[str, str]] = ...,
-        debug: Optional[int] = ...,
-        errorlevel: Optional[int] = ...,
+        pax_headers: Mapping[str, str] | None = ...,
+        debug: int | None = ...,
+        errorlevel: int | None = ...,
     ) -> TarFile: ...
     @classmethod
     def taropen(
         cls,
-        name: Optional[Text],
+        name: Text | None,
         mode: str = ...,
-        fileobj: Optional[IO[bytes]] = ...,
+        fileobj: IO[bytes] | None = ...,
         *,
         compresslevel: int = ...,
-        format: Optional[int] = ...,
-        tarinfo: Optional[Type[TarInfo]] = ...,
-        dereference: Optional[bool] = ...,
-        ignore_zeros: Optional[bool] = ...,
-        encoding: Optional[str] = ...,
-        pax_headers: Optional[Mapping[str, str]] = ...,
-        debug: Optional[int] = ...,
-        errorlevel: Optional[int] = ...,
+        format: int | None = ...,
+        tarinfo: Type[TarInfo] | None = ...,
+        dereference: bool | None = ...,
+        ignore_zeros: bool | None = ...,
+        encoding: str | None = ...,
+        pax_headers: Mapping[str, str] | None = ...,
+        debug: int | None = ...,
+        errorlevel: int | None = ...,
     ) -> TarFile: ...
     @classmethod
     def gzopen(
         cls,
-        name: Optional[Text],
+        name: Text | None,
         mode: str = ...,
-        fileobj: Optional[IO[bytes]] = ...,
+        fileobj: IO[bytes] | None = ...,
         compresslevel: int = ...,
         *,
-        format: Optional[int] = ...,
-        tarinfo: Optional[Type[TarInfo]] = ...,
-        dereference: Optional[bool] = ...,
-        ignore_zeros: Optional[bool] = ...,
-        encoding: Optional[str] = ...,
-        pax_headers: Optional[Mapping[str, str]] = ...,
-        debug: Optional[int] = ...,
-        errorlevel: Optional[int] = ...,
+        format: int | None = ...,
+        tarinfo: Type[TarInfo] | None = ...,
+        dereference: bool | None = ...,
+        ignore_zeros: bool | None = ...,
+        encoding: str | None = ...,
+        pax_headers: Mapping[str, str] | None = ...,
+        debug: int | None = ...,
+        errorlevel: int | None = ...,
     ) -> TarFile: ...
     @classmethod
     def bz2open(
         cls,
-        name: Optional[Text],
+        name: Text | None,
         mode: str = ...,
-        fileobj: Optional[IO[bytes]] = ...,
+        fileobj: IO[bytes] | None = ...,
         compresslevel: int = ...,
         *,
-        format: Optional[int] = ...,
-        tarinfo: Optional[Type[TarInfo]] = ...,
-        dereference: Optional[bool] = ...,
-        ignore_zeros: Optional[bool] = ...,
-        encoding: Optional[str] = ...,
-        pax_headers: Optional[Mapping[str, str]] = ...,
-        debug: Optional[int] = ...,
-        errorlevel: Optional[int] = ...,
+        format: int | None = ...,
+        tarinfo: Type[TarInfo] | None = ...,
+        dereference: bool | None = ...,
+        ignore_zeros: bool | None = ...,
+        encoding: str | None = ...,
+        pax_headers: Mapping[str, str] | None = ...,
+        debug: int | None = ...,
+        errorlevel: int | None = ...,
     ) -> TarFile: ...
     @classmethod
     def xzopen(
         cls,
-        name: Optional[Text],
+        name: Text | None,
         mode: str = ...,
-        fileobj: Optional[IO[bytes]] = ...,
-        preset: Optional[int] = ...,
+        fileobj: IO[bytes] | None = ...,
+        preset: int | None = ...,
         *,
-        format: Optional[int] = ...,
-        tarinfo: Optional[Type[TarInfo]] = ...,
-        dereference: Optional[bool] = ...,
-        ignore_zeros: Optional[bool] = ...,
-        encoding: Optional[str] = ...,
-        pax_headers: Optional[Mapping[str, str]] = ...,
-        debug: Optional[int] = ...,
-        errorlevel: Optional[int] = ...,
+        format: int | None = ...,
+        tarinfo: Type[TarInfo] | None = ...,
+        dereference: bool | None = ...,
+        ignore_zeros: bool | None = ...,
+        encoding: str | None = ...,
+        pax_headers: Mapping[str, str] | None = ...,
+        debug: int | None = ...,
+        errorlevel: int | None = ...,
     ) -> TarFile: ...
     def getmember(self, name: str) -> TarInfo: ...
     def getmembers(self) -> List[TarInfo]: ...
     def getnames(self) -> List[str]: ...
     def list(self, verbose: bool = ...) -> None: ...
-    def next(self) -> Optional[TarInfo]: ...
-    def extractall(self, path: Text = ..., members: Optional[Iterable[TarInfo]] = ...) -> None: ...
-    def extract(self, member: Union[str, TarInfo], path: Text = ...) -> None: ...
-    def extractfile(self, member: Union[str, TarInfo]) -> Optional[IO[bytes]]: ...
+    def next(self) -> TarInfo | None: ...
+    def extractall(self, path: Text = ..., members: Iterable[TarInfo] | None = ...) -> None: ...
+    def extract(self, member: str | TarInfo, path: Text = ...) -> None: ...
+    def extractfile(self, member: str | TarInfo) -> IO[bytes] | None: ...
     def makedir(self, tarinfo: TarInfo, targetpath: Text) -> None: ...  # undocumented
     def makefile(self, tarinfo: TarInfo, targetpath: Text) -> None: ...  # undocumented
     def makeunknown(self, tarinfo: TarInfo, targetpath: Text) -> None: ...  # undocumented
@@ -214,15 +214,13 @@ class TarFile(Iterable[TarInfo]):
     def add(
         self,
         name: str,
-        arcname: Optional[str] = ...,
+        arcname: str | None = ...,
         recursive: bool = ...,
-        exclude: Optional[Callable[[str], bool]] = ...,
-        filter: Optional[Callable[[TarInfo], Optional[TarInfo]]] = ...,
+        exclude: Callable[[str], bool] | None = ...,
+        filter: Callable[[TarInfo], TarInfo | None] | None = ...,
     ) -> None: ...
-    def addfile(self, tarinfo: TarInfo, fileobj: Optional[IO[bytes]] = ...) -> None: ...
-    def gettarinfo(
-        self, name: Optional[str] = ..., arcname: Optional[str] = ..., fileobj: Optional[IO[bytes]] = ...
-    ) -> TarInfo: ...
+    def addfile(self, tarinfo: TarInfo, fileobj: IO[bytes] | None = ...) -> None: ...
+    def gettarinfo(self, name: str | None = ..., arcname: str | None = ..., fileobj: IO[bytes] | None = ...) -> TarInfo: ...
     def close(self) -> None: ...
 
 def is_tarfile(name: Text) -> bool: ...
@@ -248,8 +246,8 @@ class TarInfo:
     devminor: int
     offset: int
     offset_data: int
-    sparse: Optional[bytes]
-    tarfile: Optional[TarFile]
+    sparse: bytes | None
+    tarfile: TarFile | None
     mode: int
     type: bytes
     linkname: str
@@ -267,15 +265,15 @@ class TarInfo:
     def linkpath(self) -> str: ...
     @linkpath.setter
     def linkpath(self, linkname: str) -> None: ...
-    def get_info(self) -> Mapping[str, Union[str, int, bytes, Mapping[str, str]]]: ...
-    def tobuf(self, format: Optional[int] = ..., encoding: Optional[str] = ..., errors: str = ...) -> bytes: ...
+    def get_info(self) -> Mapping[str, str | int | bytes | Mapping[str, str]]: ...
+    def tobuf(self, format: int | None = ..., encoding: str | None = ..., errors: str = ...) -> bytes: ...
     def create_ustar_header(
-        self, info: Mapping[str, Union[str, int, bytes, Mapping[str, str]]], encoding: str, errors: str
+        self, info: Mapping[str, str | int | bytes | Mapping[str, str]], encoding: str, errors: str
     ) -> bytes: ...
     def create_gnu_header(
-        self, info: Mapping[str, Union[str, int, bytes, Mapping[str, str]]], encoding: str, errors: str
+        self, info: Mapping[str, str | int | bytes | Mapping[str, str]], encoding: str, errors: str
     ) -> bytes: ...
-    def create_pax_header(self, info: Mapping[str, Union[str, int, bytes, Mapping[str, str]]], encoding: str) -> bytes: ...
+    def create_pax_header(self, info: Mapping[str, str | int | bytes | Mapping[str, str]], encoding: str) -> bytes: ...
     @classmethod
     def create_pax_global_header(cls, pax_headers: Mapping[str, str]) -> bytes: ...
     def isfile(self) -> bool: ...
diff --git a/stdlib/@python2/telnetlib.pyi b/stdlib/@python2/telnetlib.pyi
index 388e5a8c9310..dfb01f26398e 100644
--- a/stdlib/@python2/telnetlib.pyi
+++ b/stdlib/@python2/telnetlib.pyi
@@ -1,5 +1,5 @@
 import socket
-from typing import Any, Callable, Match, Optional, Pattern, Sequence, Tuple, Union
+from typing import Any, Callable, Match, Pattern, Sequence, Tuple
 
 DEBUGLEVEL: int
 TELNET_PORT: int
@@ -81,8 +81,8 @@ EXOPL: bytes
 NOOPT: bytes
 
 class Telnet:
-    host: Optional[str]  # undocumented
-    def __init__(self, host: Optional[str] = ..., port: int = ..., timeout: float = ...) -> None: ...
+    host: str | None  # undocumented
+    def __init__(self, host: str | None = ..., port: int = ..., timeout: float = ...) -> None: ...
     def open(self, host: str, port: int = ..., timeout: float = ...) -> None: ...
     def msg(self, msg: str, *args: Any) -> None: ...
     def set_debuglevel(self, debuglevel: int) -> None: ...
@@ -90,7 +90,7 @@ class Telnet:
     def get_socket(self) -> socket.socket: ...
     def fileno(self) -> int: ...
     def write(self, buffer: bytes) -> None: ...
-    def read_until(self, match: bytes, timeout: Optional[float] = ...) -> bytes: ...
+    def read_until(self, match: bytes, timeout: float | None = ...) -> bytes: ...
     def read_all(self) -> bytes: ...
     def read_some(self) -> bytes: ...
     def read_very_eager(self) -> bytes: ...
@@ -98,7 +98,7 @@ class Telnet:
     def read_lazy(self) -> bytes: ...
     def read_very_lazy(self) -> bytes: ...
     def read_sb_data(self) -> bytes: ...
-    def set_option_negotiation_callback(self, callback: Optional[Callable[[socket.socket, bytes, bytes], Any]]) -> None: ...
+    def set_option_negotiation_callback(self, callback: Callable[[socket.socket, bytes, bytes], Any] | None) -> None: ...
     def process_rawq(self) -> None: ...
     def rawq_getchar(self) -> bytes: ...
     def fill_rawq(self) -> None: ...
@@ -107,5 +107,5 @@ class Telnet:
     def mt_interact(self) -> None: ...
     def listener(self) -> None: ...
     def expect(
-        self, list: Sequence[Union[Pattern[bytes], bytes]], timeout: Optional[float] = ...
-    ) -> Tuple[int, Optional[Match[bytes]], bytes]: ...
+        self, list: Sequence[Pattern[bytes] | bytes], timeout: float | None = ...
+    ) -> Tuple[int, Match[bytes] | None, bytes]: ...
diff --git a/stdlib/@python2/tempfile.pyi b/stdlib/@python2/tempfile.pyi
index 9ea5e2ecba60..c5f67d243ac8 100644
--- a/stdlib/@python2/tempfile.pyi
+++ b/stdlib/@python2/tempfile.pyi
@@ -1,11 +1,11 @@
 from random import Random
 from thread import LockType
-from typing import IO, Any, AnyStr, Iterable, Iterator, List, Optional, Text, Tuple, Union, overload
+from typing import IO, Any, AnyStr, Iterable, Iterator, List, Text, Tuple, overload
 
 TMP_MAX: int
 tempdir: str
 template: str
-_name_sequence: Optional[_RandomNameSequence]
+_name_sequence: _RandomNameSequence | None
 
 class _RandomNameSequence:
     characters: str = ...
@@ -24,7 +24,7 @@ class _TemporaryFileWrapper(IO[str]):
     def __init__(self, file: IO[str], name: Any, delete: bool = ...) -> None: ...
     def __del__(self) -> None: ...
     def __enter__(self) -> _TemporaryFileWrapper: ...
-    def __exit__(self, exc, value, tb) -> Optional[bool]: ...
+    def __exit__(self, exc, value, tb) -> bool | None: ...
     def __getattr__(self, name: unicode) -> Any: ...
     def close(self) -> None: ...
     def unlink(self, path: unicode) -> None: ...
@@ -43,7 +43,7 @@ class _TemporaryFileWrapper(IO[str]):
     def seek(self, offset: int, whence: int = ...) -> int: ...
     def seekable(self) -> bool: ...
     def tell(self) -> int: ...
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     def writable(self) -> bool: ...
     def write(self, s: Text) -> int: ...
     def writelines(self, lines: Iterable[str]) -> None: ...
@@ -51,34 +51,32 @@ class _TemporaryFileWrapper(IO[str]):
 # TODO text files
 
 def TemporaryFile(
-    mode: Union[bytes, unicode] = ...,
+    mode: bytes | unicode = ...,
     bufsize: int = ...,
-    suffix: Union[bytes, unicode] = ...,
-    prefix: Union[bytes, unicode] = ...,
-    dir: Optional[Union[bytes, unicode]] = ...,
+    suffix: bytes | unicode = ...,
+    prefix: bytes | unicode = ...,
+    dir: bytes | unicode | None = ...,
 ) -> _TemporaryFileWrapper: ...
 def NamedTemporaryFile(
-    mode: Union[bytes, unicode] = ...,
+    mode: bytes | unicode = ...,
     bufsize: int = ...,
-    suffix: Union[bytes, unicode] = ...,
-    prefix: Union[bytes, unicode] = ...,
-    dir: Optional[Union[bytes, unicode]] = ...,
+    suffix: bytes | unicode = ...,
+    prefix: bytes | unicode = ...,
+    dir: bytes | unicode | None = ...,
     delete: bool = ...,
 ) -> _TemporaryFileWrapper: ...
 def SpooledTemporaryFile(
     max_size: int = ...,
-    mode: Union[bytes, unicode] = ...,
+    mode: bytes | unicode = ...,
     buffering: int = ...,
-    suffix: Union[bytes, unicode] = ...,
-    prefix: Union[bytes, unicode] = ...,
-    dir: Optional[Union[bytes, unicode]] = ...,
+    suffix: bytes | unicode = ...,
+    prefix: bytes | unicode = ...,
+    dir: bytes | unicode | None = ...,
 ) -> _TemporaryFileWrapper: ...
 
 class TemporaryDirectory:
     name: Any
-    def __init__(
-        self, suffix: Union[bytes, unicode] = ..., prefix: Union[bytes, unicode] = ..., dir: Union[bytes, unicode] = ...
-    ) -> None: ...
+    def __init__(self, suffix: bytes | unicode = ..., prefix: bytes | unicode = ..., dir: bytes | unicode = ...) -> None: ...
     def cleanup(self) -> None: ...
     def __enter__(self) -> Any: ...  # Can be str or unicode
     def __exit__(self, type, value, traceback) -> None: ...
@@ -86,17 +84,17 @@ class TemporaryDirectory:
 @overload
 def mkstemp() -> Tuple[int, str]: ...
 @overload
-def mkstemp(suffix: AnyStr = ..., prefix: AnyStr = ..., dir: Optional[AnyStr] = ..., text: bool = ...) -> Tuple[int, AnyStr]: ...
+def mkstemp(suffix: AnyStr = ..., prefix: AnyStr = ..., dir: AnyStr | None = ..., text: bool = ...) -> Tuple[int, AnyStr]: ...
 @overload
 def mkdtemp() -> str: ...
 @overload
-def mkdtemp(suffix: AnyStr = ..., prefix: AnyStr = ..., dir: Optional[AnyStr] = ...) -> AnyStr: ...
+def mkdtemp(suffix: AnyStr = ..., prefix: AnyStr = ..., dir: AnyStr | None = ...) -> AnyStr: ...
 @overload
 def mktemp() -> str: ...
 @overload
-def mktemp(suffix: AnyStr = ..., prefix: AnyStr = ..., dir: Optional[AnyStr] = ...) -> AnyStr: ...
+def mktemp(suffix: AnyStr = ..., prefix: AnyStr = ..., dir: AnyStr | None = ...) -> AnyStr: ...
 def gettempdir() -> str: ...
 def gettempprefix() -> str: ...
 def _candidate_tempdir_list() -> List[str]: ...
-def _get_candidate_names() -> Optional[_RandomNameSequence]: ...
+def _get_candidate_names() -> _RandomNameSequence | None: ...
 def _get_default_tempdir() -> str: ...
diff --git a/stdlib/@python2/threading.pyi b/stdlib/@python2/threading.pyi
index bab2acdc84cd..e45a1b5c4a89 100644
--- a/stdlib/@python2/threading.pyi
+++ b/stdlib/@python2/threading.pyi
@@ -1,5 +1,5 @@
 from types import FrameType, TracebackType
-from typing import Any, Callable, Iterable, List, Mapping, Optional, Text, Type, TypeVar, Union
+from typing import Any, Callable, Iterable, List, Mapping, Optional, Text, Type, TypeVar
 
 # TODO recursive type
 _TF = Callable[[FrameType, str, Any], Optional[Callable[..., Any]]]
@@ -15,7 +15,7 @@ def current_thread() -> Thread: ...
 def currentThread() -> Thread: ...
 def enumerate() -> List[Thread]: ...
 def settrace(func: _TF) -> None: ...
-def setprofile(func: Optional[_PF]) -> None: ...
+def setprofile(func: _PF | None) -> None: ...
 def stack_size(size: int = ...) -> int: ...
 
 class ThreadError(Exception): ...
@@ -27,19 +27,19 @@ class local(object):
 
 class Thread:
     name: str
-    ident: Optional[int]
+    ident: int | None
     daemon: bool
     def __init__(
         self,
         group: None = ...,
-        target: Optional[Callable[..., Any]] = ...,
-        name: Optional[Text] = ...,
+        target: Callable[..., Any] | None = ...,
+        name: Text | None = ...,
         args: Iterable[Any] = ...,
-        kwargs: Optional[Mapping[Text, Any]] = ...,
+        kwargs: Mapping[Text, Any] | None = ...,
     ) -> None: ...
     def start(self) -> None: ...
     def run(self) -> None: ...
-    def join(self, timeout: Optional[float] = ...) -> None: ...
+    def join(self, timeout: float | None = ...) -> None: ...
     def getName(self) -> str: ...
     def setName(self, name: Text) -> None: ...
     def is_alive(self) -> bool: ...
@@ -53,8 +53,8 @@ class Lock:
     def __init__(self) -> None: ...
     def __enter__(self) -> bool: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
     def locked(self) -> bool: ...
@@ -63,22 +63,22 @@ class _RLock:
     def __init__(self) -> None: ...
     def __enter__(self) -> bool: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
 
 RLock = _RLock
 
 class Condition:
-    def __init__(self, lock: Union[Lock, _RLock, None] = ...) -> None: ...
+    def __init__(self, lock: Lock | _RLock | None = ...) -> None: ...
     def __enter__(self) -> bool: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
-    def wait(self, timeout: Optional[float] = ...) -> bool: ...
+    def wait(self, timeout: float | None = ...) -> bool: ...
     def notify(self, n: int = ...) -> None: ...
     def notify_all(self) -> None: ...
     def notifyAll(self) -> None: ...
@@ -86,8 +86,8 @@ class Condition:
 class Semaphore:
     def __init__(self, value: int = ...) -> None: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> bool | None: ...
     def acquire(self, blocking: bool = ...) -> bool: ...
     def __enter__(self, blocking: bool = ...) -> bool: ...
     def release(self) -> None: ...
@@ -100,7 +100,7 @@ class Event:
     def isSet(self) -> bool: ...
     def set(self) -> None: ...
     def clear(self) -> None: ...
-    def wait(self, timeout: Optional[float] = ...) -> bool: ...
+    def wait(self, timeout: float | None = ...) -> bool: ...
 
 class Timer(Thread):
     def __init__(
diff --git a/stdlib/@python2/time.pyi b/stdlib/@python2/time.pyi
index 0a5353fca9c6..48ae9da9c65e 100644
--- a/stdlib/@python2/time.pyi
+++ b/stdlib/@python2/time.pyi
@@ -1,5 +1,5 @@
 import sys
-from typing import Any, NamedTuple, Optional, Tuple, Union
+from typing import Any, NamedTuple, Tuple
 
 _TimeTuple = Tuple[int, int, int, int, int, int, int, int, int]
 
@@ -30,14 +30,14 @@ class struct_time(_struct_time):
     def __init__(self, o: _TimeTuple, _arg: Any = ...) -> None: ...
     def __new__(cls, o: _TimeTuple, _arg: Any = ...) -> struct_time: ...
 
-def asctime(t: Union[_TimeTuple, struct_time] = ...) -> str: ...
+def asctime(t: _TimeTuple | struct_time = ...) -> str: ...
 def clock() -> float: ...
-def ctime(secs: Optional[float] = ...) -> str: ...
-def gmtime(secs: Optional[float] = ...) -> struct_time: ...
-def localtime(secs: Optional[float] = ...) -> struct_time: ...
-def mktime(t: Union[_TimeTuple, struct_time]) -> float: ...
+def ctime(secs: float | None = ...) -> str: ...
+def gmtime(secs: float | None = ...) -> struct_time: ...
+def localtime(secs: float | None = ...) -> struct_time: ...
+def mktime(t: _TimeTuple | struct_time) -> float: ...
 def sleep(secs: float) -> None: ...
-def strftime(format: str, t: Union[_TimeTuple, struct_time] = ...) -> str: ...
+def strftime(format: str, t: _TimeTuple | struct_time = ...) -> str: ...
 def strptime(string: str, format: str = ...) -> struct_time: ...
 def time() -> float: ...
 
diff --git a/stdlib/@python2/timeit.pyi b/stdlib/@python2/timeit.pyi
index dfb6a7b731ae..ecb528725a9c 100644
--- a/stdlib/@python2/timeit.pyi
+++ b/stdlib/@python2/timeit.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, Callable, List, Optional, Sequence, Text, Union
+from typing import IO, Any, Callable, List, Sequence, Text, Union
 
 _str = Union[str, Text]
 _Timer = Callable[[], float]
@@ -8,7 +8,7 @@ default_timer: _Timer
 
 class Timer:
     def __init__(self, stmt: _stmt = ..., setup: _stmt = ..., timer: _Timer = ...) -> None: ...
-    def print_exc(self, file: Optional[IO[str]] = ...) -> None: ...
+    def print_exc(self, file: IO[str] | None = ...) -> None: ...
     def timeit(self, number: int = ...) -> float: ...
     def repeat(self, repeat: int = ..., number: int = ...) -> List[float]: ...
 
@@ -17,4 +17,4 @@ def repeat(stmt: _stmt = ..., setup: _stmt = ..., timer: _Timer = ..., repeat: i
 
 _timerFunc = Callable[[], float]
 
-def main(args: Optional[Sequence[str]] = ..., *, _wrap_timer: Optional[Callable[[_timerFunc], _timerFunc]] = ...) -> None: ...
+def main(args: Sequence[str] | None = ..., *, _wrap_timer: Callable[[_timerFunc], _timerFunc] | None = ...) -> None: ...
diff --git a/stdlib/@python2/trace.pyi b/stdlib/@python2/trace.pyi
index 810639869e20..62f228673a55 100644
--- a/stdlib/@python2/trace.pyi
+++ b/stdlib/@python2/trace.pyi
@@ -1,6 +1,6 @@
 import types
 from _typeshed import StrPath
-from typing import Any, Callable, Dict, Mapping, Optional, Sequence, Tuple, TypeVar, Union
+from typing import Any, Callable, Dict, Mapping, Optional, Sequence, Tuple, TypeVar
 
 _T = TypeVar("_T")
 _localtrace = Callable[[types.FrameType, str, Any], Callable[..., Any]]
@@ -9,16 +9,16 @@ _fileModuleFunction = Tuple[str, Optional[str], str]
 class CoverageResults:
     def __init__(
         self,
-        counts: Optional[Dict[Tuple[str, int], int]] = ...,
-        calledfuncs: Optional[Dict[_fileModuleFunction, int]] = ...,
-        infile: Optional[StrPath] = ...,
-        callers: Optional[Dict[Tuple[_fileModuleFunction, _fileModuleFunction], int]] = ...,
-        outfile: Optional[StrPath] = ...,
+        counts: Dict[Tuple[str, int], int] | None = ...,
+        calledfuncs: Dict[_fileModuleFunction, int] | None = ...,
+        infile: StrPath | None = ...,
+        callers: Dict[Tuple[_fileModuleFunction, _fileModuleFunction], int] | None = ...,
+        outfile: StrPath | None = ...,
     ) -> None: ...  # undocumented
     def update(self, other: CoverageResults) -> None: ...
-    def write_results(self, show_missing: bool = ..., summary: bool = ..., coverdir: Optional[StrPath] = ...) -> None: ...
+    def write_results(self, show_missing: bool = ..., summary: bool = ..., coverdir: StrPath | None = ...) -> None: ...
     def write_results_file(
-        self, path: StrPath, lines: Sequence[str], lnotab: Any, lines_hit: Mapping[int, int], encoding: Optional[str] = ...
+        self, path: StrPath, lines: Sequence[str], lnotab: Any, lines_hit: Mapping[int, int], encoding: str | None = ...
     ) -> Tuple[int, int]: ...
 
 class Trace:
@@ -30,16 +30,13 @@ class Trace:
         countcallers: int = ...,
         ignoremods: Sequence[str] = ...,
         ignoredirs: Sequence[str] = ...,
-        infile: Optional[StrPath] = ...,
-        outfile: Optional[StrPath] = ...,
+        infile: StrPath | None = ...,
+        outfile: StrPath | None = ...,
         timing: bool = ...,
     ) -> None: ...
-    def run(self, cmd: Union[str, types.CodeType]) -> None: ...
+    def run(self, cmd: str | types.CodeType) -> None: ...
     def runctx(
-        self,
-        cmd: Union[str, types.CodeType],
-        globals: Optional[Mapping[str, Any]] = ...,
-        locals: Optional[Mapping[str, Any]] = ...,
+        self, cmd: str | types.CodeType, globals: Mapping[str, Any] | None = ..., locals: Mapping[str, Any] | None = ...
     ) -> None: ...
     def runfunc(self, func: Callable[..., _T], *args: Any, **kw: Any) -> _T: ...
     def file_module_function_of(self, frame: types.FrameType) -> _fileModuleFunction: ...
diff --git a/stdlib/@python2/traceback.pyi b/stdlib/@python2/traceback.pyi
index 3144fdd6700b..2152ab255942 100644
--- a/stdlib/@python2/traceback.pyi
+++ b/stdlib/@python2/traceback.pyi
@@ -3,25 +3,25 @@ from typing import IO, List, Optional, Tuple, Type
 
 _PT = Tuple[str, int, str, Optional[str]]
 
-def print_tb(tb: Optional[TracebackType], limit: Optional[int] = ..., file: Optional[IO[str]] = ...) -> None: ...
+def print_tb(tb: TracebackType | None, limit: int | None = ..., file: IO[str] | None = ...) -> None: ...
 def print_exception(
-    etype: Optional[Type[BaseException]],
-    value: Optional[BaseException],
-    tb: Optional[TracebackType],
-    limit: Optional[int] = ...,
-    file: Optional[IO[str]] = ...,
+    etype: Type[BaseException] | None,
+    value: BaseException | None,
+    tb: TracebackType | None,
+    limit: int | None = ...,
+    file: IO[str] | None = ...,
 ) -> None: ...
-def print_exc(limit: Optional[int] = ..., file: Optional[IO[str]] = ...) -> None: ...
-def print_last(limit: Optional[int] = ..., file: Optional[IO[str]] = ...) -> None: ...
-def print_stack(f: Optional[FrameType] = ..., limit: Optional[int] = ..., file: Optional[IO[str]] = ...) -> None: ...
-def extract_tb(tb: Optional[TracebackType], limit: Optional[int] = ...) -> List[_PT]: ...
-def extract_stack(f: Optional[FrameType] = ..., limit: Optional[int] = ...) -> List[_PT]: ...
+def print_exc(limit: int | None = ..., file: IO[str] | None = ...) -> None: ...
+def print_last(limit: int | None = ..., file: IO[str] | None = ...) -> None: ...
+def print_stack(f: FrameType | None = ..., limit: int | None = ..., file: IO[str] | None = ...) -> None: ...
+def extract_tb(tb: TracebackType | None, limit: int | None = ...) -> List[_PT]: ...
+def extract_stack(f: FrameType | None = ..., limit: int | None = ...) -> List[_PT]: ...
 def format_list(extracted_list: List[_PT]) -> List[str]: ...
-def format_exception_only(etype: Optional[Type[BaseException]], value: Optional[BaseException]) -> List[str]: ...
+def format_exception_only(etype: Type[BaseException] | None, value: BaseException | None) -> List[str]: ...
 def format_exception(
-    etype: Optional[Type[BaseException]], value: Optional[BaseException], tb: Optional[TracebackType], limit: Optional[int] = ...
+    etype: Type[BaseException] | None, value: BaseException | None, tb: TracebackType | None, limit: int | None = ...
 ) -> List[str]: ...
-def format_exc(limit: Optional[int] = ...) -> str: ...
-def format_tb(tb: Optional[TracebackType], limit: Optional[int] = ...) -> List[str]: ...
-def format_stack(f: Optional[FrameType] = ..., limit: Optional[int] = ...) -> List[str]: ...
+def format_exc(limit: int | None = ...) -> str: ...
+def format_tb(tb: TracebackType | None, limit: int | None = ...) -> List[str]: ...
+def format_stack(f: FrameType | None = ..., limit: int | None = ...) -> List[str]: ...
 def tb_lineno(tb: TracebackType) -> int: ...
diff --git a/stdlib/@python2/turtle.pyi b/stdlib/@python2/turtle.pyi
index 6476c9de04ff..659dfd31b161 100644
--- a/stdlib/@python2/turtle.pyi
+++ b/stdlib/@python2/turtle.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, Dict, List, Optional, Sequence, Text, Tuple, TypeVar, Union, overload
+from typing import Any, Callable, Dict, List, Sequence, Text, Tuple, TypeVar, Union, overload
 
 # TODO: Replace these aliases once we have Python 2 stubs for the Tkinter module.
 Canvas = Any
@@ -33,8 +33,8 @@ class Terminator(Exception): ...
 class TurtleGraphicsError(Exception): ...
 
 class Shape(object):
-    def __init__(self, type_: str, data: Union[_PolygonCoords, PhotoImage, None] = ...) -> None: ...
-    def addcomponent(self, poly: _PolygonCoords, fill: _Color, outline: Optional[_Color] = ...) -> None: ...
+    def __init__(self, type_: str, data: _PolygonCoords | PhotoImage | None = ...) -> None: ...
+    def addcomponent(self, poly: _PolygonCoords, fill: _Color, outline: _Color | None = ...) -> None: ...
 
 class TurtleScreen(TurtleScreenBase):
     def __init__(self, cv: Canvas, mode: str = ..., colormode: float = ..., delay: int = ...) -> None: ...
@@ -44,7 +44,7 @@ class TurtleScreen(TurtleScreenBase):
     @overload
     def mode(self, mode: str) -> None: ...
     def setworldcoordinates(self, llx: float, lly: float, urx: float, ury: float) -> None: ...
-    def register_shape(self, name: str, shape: Union[_PolygonCoords, Shape, None] = ...) -> None: ...
+    def register_shape(self, name: str, shape: _PolygonCoords | Shape | None = ...) -> None: ...
     @overload
     def colormode(self, cmode: None = ...) -> float: ...
     @overload
@@ -60,7 +60,7 @@ class TurtleScreen(TurtleScreenBase):
     @overload
     def tracer(self, n: None = ...) -> int: ...
     @overload
-    def tracer(self, n: int, delay: Optional[int] = ...) -> None: ...
+    def tracer(self, n: int, delay: int | None = ...) -> None: ...
     @overload
     def delay(self, delay: None = ...) -> int: ...
     @overload
@@ -70,9 +70,9 @@ class TurtleScreen(TurtleScreenBase):
     def window_height(self) -> int: ...
     def getcanvas(self) -> Canvas: ...
     def getshapes(self) -> List[str]: ...
-    def onclick(self, fun: Callable[[float, float], Any], btn: int = ..., add: Optional[Any] = ...) -> None: ...
+    def onclick(self, fun: Callable[[float, float], Any], btn: int = ..., add: Any | None = ...) -> None: ...
     def onkey(self, fun: Callable[[], Any], key: str) -> None: ...
-    def listen(self, xdummy: Optional[float] = ..., ydummy: Optional[float] = ...) -> None: ...
+    def listen(self, xdummy: float | None = ..., ydummy: float | None = ...) -> None: ...
     def ontimer(self, fun: Callable[[], Any], t: int = ...) -> None: ...
     @overload
     def bgpic(self, picname: None = ...) -> str: ...
@@ -82,7 +82,7 @@ class TurtleScreen(TurtleScreenBase):
     def screensize(self, canvwidth: None = ..., canvheight: None = ..., bg: None = ...) -> Tuple[int, int]: ...
     # Looks like if self.cv is not a ScrolledCanvas, this could return a tuple as well
     @overload
-    def screensize(self, canvwidth: int, canvheight: int, bg: Optional[_Color] = ...) -> None: ...
+    def screensize(self, canvwidth: int, canvheight: int, bg: _Color | None = ...) -> None: ...
     onscreenclick = onclick
     resetscreen = reset
     clearscreen = clear
@@ -112,16 +112,16 @@ class TNavigator(object):
     def setx(self, x: float) -> None: ...
     def sety(self, y: float) -> None: ...
     @overload
-    def distance(self, x: Union[TNavigator, Tuple[float, float]], y: None = ...) -> float: ...
+    def distance(self, x: TNavigator | Tuple[float, float], y: None = ...) -> float: ...
     @overload
     def distance(self, x: float, y: float) -> float: ...
     @overload
-    def towards(self, x: Union[TNavigator, Tuple[float, float]], y: None = ...) -> float: ...
+    def towards(self, x: TNavigator | Tuple[float, float], y: None = ...) -> float: ...
     @overload
     def towards(self, x: float, y: float) -> float: ...
     def heading(self) -> float: ...
     def setheading(self, to_angle: float) -> None: ...
-    def circle(self, radius: float, extent: Optional[float] = ..., steps: Optional[int] = ...) -> None: ...
+    def circle(self, radius: float, extent: float | None = ..., steps: int | None = ...) -> None: ...
     fd = forward
     bk = back
     backward = back
@@ -178,7 +178,7 @@ class TPen(object):
     @overload
     def pen(
         self,
-        pen: Optional[_PenState] = ...,
+        pen: _PenState | None = ...,
         *,
         shown: bool = ...,
         pendown: bool = ...,
@@ -203,10 +203,10 @@ _T = TypeVar("_T")
 
 class RawTurtle(TPen, TNavigator):
     def __init__(
-        self, canvas: Union[Canvas, TurtleScreen, None] = ..., shape: str = ..., undobuffersize: int = ..., visible: bool = ...
+        self, canvas: Canvas | TurtleScreen | None = ..., shape: str = ..., undobuffersize: int = ..., visible: bool = ...
     ) -> None: ...
     def reset(self) -> None: ...
-    def setundobuffer(self, size: Optional[int]) -> None: ...
+    def setundobuffer(self, size: int | None) -> None: ...
     def undobufferentries(self) -> int: ...
     def clear(self) -> None: ...
     def clone(self: _T) -> _T: ...
@@ -219,7 +219,7 @@ class RawTurtle(TPen, TNavigator):
     def shapesize(self) -> Tuple[float, float, float]: ...  # type: ignore
     @overload
     def shapesize(
-        self, stretch_wid: Optional[float] = ..., stretch_len: Optional[float] = ..., outline: Optional[float] = ...
+        self, stretch_wid: float | None = ..., stretch_len: float | None = ..., outline: float | None = ...
     ) -> None: ...
     def settiltangle(self, angle: float) -> None: ...
     @overload
@@ -231,22 +231,22 @@ class RawTurtle(TPen, TNavigator):
     # a compound stamp or not. So, as per the "no Union return" policy,
     # we return Any.
     def stamp(self) -> Any: ...
-    def clearstamp(self, stampid: Union[int, Tuple[int, ...]]) -> None: ...
-    def clearstamps(self, n: Optional[int] = ...) -> None: ...
+    def clearstamp(self, stampid: int | Tuple[int, ...]) -> None: ...
+    def clearstamps(self, n: int | None = ...) -> None: ...
     def filling(self) -> bool: ...
     def begin_fill(self) -> None: ...
     def end_fill(self) -> None: ...
-    def dot(self, size: Optional[int] = ..., *color: _Color) -> None: ...
+    def dot(self, size: int | None = ..., *color: _Color) -> None: ...
     def write(self, arg: object, move: bool = ..., align: str = ..., font: Tuple[str, int, str] = ...) -> None: ...
     def begin_poly(self) -> None: ...
     def end_poly(self) -> None: ...
-    def get_poly(self) -> Optional[_PolygonCoords]: ...
+    def get_poly(self) -> _PolygonCoords | None: ...
     def getscreen(self) -> TurtleScreen: ...
     def getturtle(self: _T) -> _T: ...
     getpen = getturtle
-    def onclick(self, fun: Callable[[float, float], Any], btn: int = ..., add: Optional[bool] = ...) -> None: ...
-    def onrelease(self, fun: Callable[[float, float], Any], btn: int = ..., add: Optional[bool] = ...) -> None: ...
-    def ondrag(self, fun: Callable[[float, float], Any], btn: int = ..., add: Optional[bool] = ...) -> None: ...
+    def onclick(self, fun: Callable[[float, float], Any], btn: int = ..., add: bool | None = ...) -> None: ...
+    def onrelease(self, fun: Callable[[float, float], Any], btn: int = ..., add: bool | None = ...) -> None: ...
+    def ondrag(self, fun: Callable[[float, float], Any], btn: int = ..., add: bool | None = ...) -> None: ...
     def undo(self) -> None: ...
     turtlesize = shapesize
 
@@ -254,11 +254,7 @@ class _Screen(TurtleScreen):
     def __init__(self) -> None: ...
     # Note int and float are interpreted differently, hence the Union instead of just float
     def setup(
-        self,
-        width: Union[int, float] = ...,
-        height: Union[int, float] = ...,
-        startx: Optional[int] = ...,
-        starty: Optional[int] = ...,
+        self, width: int | float = ..., height: int | float = ..., startx: int | None = ..., starty: int | None = ...
     ) -> None: ...
     def title(self, titlestring: str) -> None: ...
     def bye(self) -> None: ...
@@ -295,7 +291,7 @@ def mode(mode: None = ...) -> str: ...
 @overload
 def mode(mode: str) -> None: ...
 def setworldcoordinates(llx: float, lly: float, urx: float, ury: float) -> None: ...
-def register_shape(name: str, shape: Union[_PolygonCoords, Shape, None] = ...) -> None: ...
+def register_shape(name: str, shape: _PolygonCoords | Shape | None = ...) -> None: ...
 @overload
 def colormode(cmode: None = ...) -> float: ...
 @overload
@@ -311,7 +307,7 @@ def bgcolor(r: float, g: float, b: float) -> None: ...
 @overload
 def tracer(n: None = ...) -> int: ...
 @overload
-def tracer(n: int, delay: Optional[int] = ...) -> None: ...
+def tracer(n: int, delay: int | None = ...) -> None: ...
 @overload
 def delay(delay: None = ...) -> int: ...
 @overload
@@ -321,9 +317,9 @@ def window_width() -> int: ...
 def window_height() -> int: ...
 def getcanvas() -> Canvas: ...
 def getshapes() -> List[str]: ...
-def onclick(fun: Callable[[float, float], Any], btn: int = ..., add: Optional[Any] = ...) -> None: ...
+def onclick(fun: Callable[[float, float], Any], btn: int = ..., add: Any | None = ...) -> None: ...
 def onkey(fun: Callable[[], Any], key: str) -> None: ...
-def listen(xdummy: Optional[float] = ..., ydummy: Optional[float] = ...) -> None: ...
+def listen(xdummy: float | None = ..., ydummy: float | None = ...) -> None: ...
 def ontimer(fun: Callable[[], Any], t: int = ...) -> None: ...
 @overload
 def bgpic(picname: None = ...) -> str: ...
@@ -332,7 +328,7 @@ def bgpic(picname: str) -> None: ...
 @overload
 def screensize(canvwidth: None = ..., canvheight: None = ..., bg: None = ...) -> Tuple[int, int]: ...
 @overload
-def screensize(canvwidth: int, canvheight: int, bg: Optional[_Color] = ...) -> None: ...
+def screensize(canvwidth: int, canvheight: int, bg: _Color | None = ...) -> None: ...
 
 onscreenclick = onclick
 resetscreen = reset
@@ -340,7 +336,7 @@ clearscreen = clear
 addshape = register_shape
 # Functions copied from _Screen:
 
-def setup(width: float = ..., height: float = ..., startx: Optional[int] = ..., starty: Optional[int] = ...) -> None: ...
+def setup(width: float = ..., height: float = ..., startx: int | None = ..., starty: int | None = ...) -> None: ...
 def title(titlestring: str) -> None: ...
 def bye() -> None: ...
 def exitonclick() -> None: ...
@@ -365,16 +361,16 @@ def home() -> None: ...
 def setx(x: float) -> None: ...
 def sety(y: float) -> None: ...
 @overload
-def distance(x: Union[TNavigator, Tuple[float, float]], y: None = ...) -> float: ...
+def distance(x: TNavigator | Tuple[float, float], y: None = ...) -> float: ...
 @overload
 def distance(x: float, y: float) -> float: ...
 @overload
-def towards(x: Union[TNavigator, Tuple[float, float]], y: None = ...) -> float: ...
+def towards(x: TNavigator | Tuple[float, float], y: None = ...) -> float: ...
 @overload
 def towards(x: float, y: float) -> float: ...
 def heading() -> float: ...
 def setheading(to_angle: float) -> None: ...
-def circle(radius: float, extent: Optional[float] = ..., steps: Optional[int] = ...) -> None: ...
+def circle(radius: float, extent: float | None = ..., steps: int | None = ...) -> None: ...
 
 fd = forward
 bk = back
@@ -431,7 +427,7 @@ def isvisible() -> bool: ...
 def pen() -> _PenState: ...  # type: ignore
 @overload
 def pen(
-    pen: Optional[_PenState] = ...,
+    pen: _PenState | None = ...,
     *,
     shown: bool = ...,
     pendown: bool = ...,
@@ -455,7 +451,7 @@ ht = hideturtle
 
 # Functions copied from RawTurtle:
 
-def setundobuffer(size: Optional[int]) -> None: ...
+def setundobuffer(size: int | None) -> None: ...
 def undobufferentries() -> int: ...
 @overload
 def shape(name: None = ...) -> str: ...
@@ -466,7 +462,7 @@ def shape(name: str) -> None: ...
 @overload
 def shapesize() -> Tuple[float, float, float]: ...  # type: ignore
 @overload
-def shapesize(stretch_wid: Optional[float] = ..., stretch_len: Optional[float] = ..., outline: Optional[float] = ...) -> None: ...
+def shapesize(stretch_wid: float | None = ..., stretch_len: float | None = ..., outline: float | None = ...) -> None: ...
 def settiltangle(angle: float) -> None: ...
 @overload
 def tiltangle(angle: None = ...) -> float: ...
@@ -478,23 +474,23 @@ def tilt(angle: float) -> None: ...
 # a compound stamp or not. So, as per the "no Union return" policy,
 # we return Any.
 def stamp() -> Any: ...
-def clearstamp(stampid: Union[int, Tuple[int, ...]]) -> None: ...
-def clearstamps(n: Optional[int] = ...) -> None: ...
+def clearstamp(stampid: int | Tuple[int, ...]) -> None: ...
+def clearstamps(n: int | None = ...) -> None: ...
 def filling() -> bool: ...
 def begin_fill() -> None: ...
 def end_fill() -> None: ...
-def dot(size: Optional[int] = ..., *color: _Color) -> None: ...
+def dot(size: int | None = ..., *color: _Color) -> None: ...
 def write(arg: object, move: bool = ..., align: str = ..., font: Tuple[str, int, str] = ...) -> None: ...
 def begin_poly() -> None: ...
 def end_poly() -> None: ...
-def get_poly() -> Optional[_PolygonCoords]: ...
+def get_poly() -> _PolygonCoords | None: ...
 def getscreen() -> TurtleScreen: ...
 def getturtle() -> Turtle: ...
 
 getpen = getturtle
 
-def onrelease(fun: Callable[[float, float], Any], btn: int = ..., add: Optional[Any] = ...) -> None: ...
-def ondrag(fun: Callable[[float, float], Any], btn: int = ..., add: Optional[Any] = ...) -> None: ...
+def onrelease(fun: Callable[[float, float], Any], btn: int = ..., add: Any | None = ...) -> None: ...
+def ondrag(fun: Callable[[float, float], Any], btn: int = ..., add: Any | None = ...) -> None: ...
 def undo() -> None: ...
 
 turtlesize = shapesize
diff --git a/stdlib/@python2/types.pyi b/stdlib/@python2/types.pyi
index cf57c6329665..72b9321a860f 100644
--- a/stdlib/@python2/types.pyi
+++ b/stdlib/@python2/types.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Callable, Dict, Iterable, Iterator, List, Optional, Tuple, Type, TypeVar, Union, overload
+from typing import Any, Callable, Dict, Iterable, Iterator, List, Tuple, Type, TypeVar, overload
 
 _T = TypeVar("_T")
 
@@ -27,11 +27,11 @@ class _Cell:
     cell_contents: Any
 
 class FunctionType:
-    func_closure: Optional[Tuple[_Cell, ...]] = ...
+    func_closure: Tuple[_Cell, ...] | None = ...
     func_code: CodeType = ...
-    func_defaults: Optional[Tuple[Any, ...]] = ...
+    func_defaults: Tuple[Any, ...] | None = ...
     func_dict: Dict[str, Any] = ...
-    func_doc: Optional[str] = ...
+    func_doc: str | None = ...
     func_globals: Dict[str, Any] = ...
     func_name: str = ...
     __closure__ = func_closure
@@ -44,12 +44,12 @@ class FunctionType:
         self,
         code: CodeType,
         globals: Dict[str, Any],
-        name: Optional[str] = ...,
-        argdefs: Optional[Tuple[object, ...]] = ...,
-        closure: Optional[Tuple[_Cell, ...]] = ...,
+        name: str | None = ...,
+        argdefs: Tuple[object, ...] | None = ...,
+        closure: Tuple[_Cell, ...] | None = ...,
     ) -> None: ...
     def __call__(self, *args: Any, **kwargs: Any) -> Any: ...
-    def __get__(self, obj: Optional[object], type: Optional[type]) -> UnboundMethodType: ...
+    def __get__(self, obj: object | None, type: type | None) -> UnboundMethodType: ...
 
 LambdaType = FunctionType
 
@@ -95,11 +95,9 @@ class GeneratorType:
     def next(self) -> Any: ...
     def send(self, __arg: Any) -> Any: ...
     @overload
-    def throw(
-        self, __typ: Type[BaseException], __val: Union[BaseException, object] = ..., __tb: Optional[TracebackType] = ...
-    ) -> Any: ...
+    def throw(self, __typ: Type[BaseException], __val: BaseException | object = ..., __tb: TracebackType | None = ...) -> Any: ...
     @overload
-    def throw(self, __typ: BaseException, __val: None = ..., __tb: Optional[TracebackType] = ...) -> Any: ...
+    def throw(self, __typ: BaseException, __val: None = ..., __tb: TracebackType | None = ...) -> Any: ...
 
 class ClassType: ...
 
@@ -118,19 +116,19 @@ class InstanceType(object): ...
 MethodType = UnboundMethodType
 
 class BuiltinFunctionType:
-    __self__: Optional[object]
+    __self__: object | None
     def __call__(self, *args: Any, **kwargs: Any) -> Any: ...
 
 BuiltinMethodType = BuiltinFunctionType
 
 class ModuleType:
-    __doc__: Optional[str]
-    __file__: Optional[str]
+    __doc__: str | None
+    __file__: str | None
     __name__: str
-    __package__: Optional[str]
-    __path__: Optional[Iterable[str]]
+    __package__: str | None
+    __path__: Iterable[str] | None
     __dict__: Dict[str, Any]
-    def __init__(self, name: str, doc: Optional[str] = ...) -> None: ...
+    def __init__(self, name: str, doc: str | None = ...) -> None: ...
 
 FileType = file
 XRangeType = xrange
@@ -164,7 +162,7 @@ class DictProxyType:
     # TODO is it possible to have non-string keys?
     # no __init__
     def copy(self) -> Dict[Any, Any]: ...
-    def get(self, key: str, default: _T = ...) -> Union[Any, _T]: ...
+    def get(self, key: str, default: _T = ...) -> Any | _T: ...
     def has_key(self, key: str) -> bool: ...
     def items(self) -> List[Tuple[str, Any]]: ...
     def iteritems(self) -> Iterator[Tuple[str, Any]]: ...
diff --git a/stdlib/@python2/typing.pyi b/stdlib/@python2/typing.pyi
index dfcac95197b0..a1b02e81990c 100644
--- a/stdlib/@python2/typing.pyi
+++ b/stdlib/@python2/typing.pyi
@@ -9,17 +9,12 @@ Any = object()
 
 class TypeVar:
     __name__: str
-    __bound__: Optional[Type[Any]]
+    __bound__: Type[Any] | None
     __constraints__: Tuple[Type[Any], ...]
     __covariant__: bool
     __contravariant__: bool
     def __init__(
-        self,
-        name: str,
-        *constraints: Type[Any],
-        bound: Optional[Type[Any]] = ...,
-        covariant: bool = ...,
-        contravariant: bool = ...,
+        self, name: str, *constraints: Type[Any], bound: Type[Any] | None = ..., covariant: bool = ..., contravariant: bool = ...
     ) -> None: ...
 
 _promote = object()
@@ -144,11 +139,11 @@ class Generator(Iterator[_T_co], Generic[_T_co, _T_contra, _V_co]):
     @overload
     @abstractmethod
     def throw(
-        self, __typ: Type[BaseException], __val: Union[BaseException, object] = ..., __tb: Optional[TracebackType] = ...
+        self, __typ: Type[BaseException], __val: BaseException | object = ..., __tb: TracebackType | None = ...
     ) -> _T_co: ...
     @overload
     @abstractmethod
-    def throw(self, __typ: BaseException, __val: None = ..., __tb: Optional[TracebackType] = ...) -> _T_co: ...
+    def throw(self, __typ: BaseException, __val: None = ..., __tb: TracebackType | None = ...) -> _T_co: ...
     @abstractmethod
     def close(self) -> None: ...
     @property
@@ -218,9 +213,9 @@ class AbstractSet(Iterable[_T_co], Container[_T_co], Generic[_T_co]):
     def __gt__(self, s: AbstractSet[Any]) -> bool: ...
     def __ge__(self, s: AbstractSet[Any]) -> bool: ...
     def __and__(self, s: AbstractSet[Any]) -> AbstractSet[_T_co]: ...
-    def __or__(self, s: AbstractSet[_T]) -> AbstractSet[Union[_T_co, _T]]: ...
+    def __or__(self, s: AbstractSet[_T]) -> AbstractSet[_T_co | _T]: ...
     def __sub__(self, s: AbstractSet[Any]) -> AbstractSet[_T_co]: ...
-    def __xor__(self, s: AbstractSet[_T]) -> AbstractSet[Union[_T_co, _T]]: ...
+    def __xor__(self, s: AbstractSet[_T]) -> AbstractSet[_T_co | _T]: ...
     # TODO: argument can be any container?
     def isdisjoint(self, s: AbstractSet[Any]) -> bool: ...
     # Implement Sized (but don't have it as a base class).
@@ -236,9 +231,9 @@ class MutableSet(AbstractSet[_T], Generic[_T]):
     def clear(self) -> None: ...
     def pop(self) -> _T: ...
     def remove(self, element: _T) -> None: ...
-    def __ior__(self, s: AbstractSet[_S]) -> MutableSet[Union[_T, _S]]: ...
+    def __ior__(self, s: AbstractSet[_S]) -> MutableSet[_T | _S]: ...
     def __iand__(self, s: AbstractSet[Any]) -> MutableSet[_T]: ...
-    def __ixor__(self, s: AbstractSet[_S]) -> MutableSet[Union[_T, _S]]: ...
+    def __ixor__(self, s: AbstractSet[_S]) -> MutableSet[_T | _S]: ...
     def __isub__(self, s: AbstractSet[Any]) -> MutableSet[_T]: ...
 
 class MappingView(object):
@@ -263,11 +258,8 @@ class ValuesView(MappingView, Iterable[_VT_co], Generic[_VT_co]):
 class ContextManager(Protocol[_T_co]):
     def __enter__(self) -> _T_co: ...
     def __exit__(
-        self,
-        __exc_type: Optional[Type[BaseException]],
-        __exc_value: Optional[BaseException],
-        __traceback: Optional[TracebackType],
-    ) -> Optional[bool]: ...
+        self, __exc_type: Type[BaseException] | None, __exc_value: BaseException | None, __traceback: TracebackType | None
+    ) -> bool | None: ...
 
 class Mapping(Iterable[_KT], Container[_KT], Generic[_KT, _VT_co]):
     # TODO: We wish the key type could also be covariant, but that doesn't work,
@@ -276,9 +268,9 @@ class Mapping(Iterable[_KT], Container[_KT], Generic[_KT, _VT_co]):
     def __getitem__(self, k: _KT) -> _VT_co: ...
     # Mixin methods
     @overload
-    def get(self, k: _KT) -> Optional[_VT_co]: ...
+    def get(self, k: _KT) -> _VT_co | None: ...
     @overload
-    def get(self, k: _KT, default: Union[_VT_co, _T]) -> Union[_VT_co, _T]: ...
+    def get(self, k: _KT, default: _VT_co | _T) -> _VT_co | _T: ...
     def keys(self) -> list[_KT]: ...
     def values(self) -> list[_VT_co]: ...
     def items(self) -> list[Tuple[_KT, _VT_co]]: ...
@@ -299,7 +291,7 @@ class MutableMapping(Mapping[_KT, _VT], Generic[_KT, _VT]):
     @overload
     def pop(self, k: _KT) -> _VT: ...
     @overload
-    def pop(self, k: _KT, default: Union[_VT, _T] = ...) -> Union[_VT, _T]: ...
+    def pop(self, k: _KT, default: _VT | _T = ...) -> _VT | _T: ...
     def popitem(self) -> Tuple[_KT, _VT]: ...
     def setdefault(self, k: _KT, default: _VT = ...) -> _VT: ...
     @overload
@@ -346,7 +338,7 @@ class IO(Iterator[AnyStr], Generic[AnyStr]):
     @abstractmethod
     def tell(self) -> int: ...
     @abstractmethod
-    def truncate(self, size: Optional[int] = ...) -> int: ...
+    def truncate(self, size: int | None = ...) -> int: ...
     @abstractmethod
     def writable(self) -> bool: ...
     # TODO buffer objects
@@ -362,8 +354,8 @@ class IO(Iterator[AnyStr], Generic[AnyStr]):
     def __enter__(self) -> IO[AnyStr]: ...
     @abstractmethod
     def __exit__(
-        self, t: Optional[Type[BaseException]], value: Optional[BaseException], traceback: Optional[TracebackType]
-    ) -> Optional[bool]: ...
+        self, t: Type[BaseException] | None, value: BaseException | None, traceback: TracebackType | None
+    ) -> bool | None: ...
 
 class BinaryIO(IO[str]):
     # TODO readinto
@@ -379,7 +371,7 @@ class TextIO(IO[unicode]):
     @property
     def encoding(self) -> str: ...
     @property
-    def errors(self) -> Optional[str]: ...
+    def errors(self) -> str | None: ...
     @property
     def line_buffering(self) -> bool: ...
     @property
@@ -392,7 +384,7 @@ class ByteString(Sequence[int], metaclass=ABCMeta): ...
 class Match(Generic[AnyStr]):
     pos: int
     endpos: int
-    lastindex: Optional[int]
+    lastindex: int | None
     string: AnyStr
 
     # The regular expression object whose match() or search() method produced
@@ -404,8 +396,8 @@ class Match(Generic[AnyStr]):
     re: Pattern[Any]
     # Can be None if there are no groups or if the last group was unnamed;
     # otherwise matches the type of the pattern.
-    lastgroup: Optional[Any]
-    def expand(self, template: Union[str, Text]) -> Any: ...
+    lastgroup: Any | None
+    def expand(self, template: str | Text) -> Any: ...
     @overload
     def group(self, group1: int = ...) -> AnyStr: ...
     @overload
@@ -416,9 +408,9 @@ class Match(Generic[AnyStr]):
     def group(self, group1: str, group2: str, *groups: str) -> Tuple[AnyStr, ...]: ...
     def groups(self, default: AnyStr = ...) -> Tuple[AnyStr, ...]: ...
     def groupdict(self, default: AnyStr = ...) -> Dict[str, AnyStr]: ...
-    def start(self, __group: Union[int, str] = ...) -> int: ...
-    def end(self, __group: Union[int, str] = ...) -> int: ...
-    def span(self, __group: Union[int, str] = ...) -> Tuple[int, int]: ...
+    def start(self, __group: int | str = ...) -> int: ...
+    def end(self, __group: int | str = ...) -> int: ...
+    def span(self, __group: int | str = ...) -> Tuple[int, int]: ...
     @property
     def regs(self) -> Tuple[Tuple[int, int], ...]: ...  # undocumented
 
@@ -433,12 +425,12 @@ class Pattern(Generic[AnyStr]):
     groupindex: Dict[AnyStr, int]
     groups: int
     pattern: AnyStr
-    def search(self, string: _AnyStr2, pos: int = ..., endpos: int = ...) -> Optional[Match[_AnyStr2]]: ...
-    def match(self, string: _AnyStr2, pos: int = ..., endpos: int = ...) -> Optional[Match[_AnyStr2]]: ...
+    def search(self, string: _AnyStr2, pos: int = ..., endpos: int = ...) -> Match[_AnyStr2] | None: ...
+    def match(self, string: _AnyStr2, pos: int = ..., endpos: int = ...) -> Match[_AnyStr2] | None: ...
     def split(self, string: _AnyStr2, maxsplit: int = ...) -> List[_AnyStr2]: ...
     # Returns either a list of _AnyStr2 or a list of tuples, depending on
     # whether there are groups in the pattern.
-    def findall(self, string: Union[bytes, Text], pos: int = ..., endpos: int = ...) -> List[Any]: ...
+    def findall(self, string: bytes | Text, pos: int = ..., endpos: int = ...) -> List[Any]: ...
     def finditer(self, string: _AnyStr2, pos: int = ..., endpos: int = ...) -> Iterator[Match[_AnyStr2]]: ...
     @overload
     def sub(self, repl: _AnyStr2, string: _AnyStr2, count: int = ...) -> _AnyStr2: ...
@@ -452,7 +444,7 @@ class Pattern(Generic[AnyStr]):
 # Functions
 
 def get_type_hints(
-    obj: Callable[..., Any], globalns: Optional[Dict[Text, Any]] = ..., localns: Optional[Dict[Text, Any]] = ...
+    obj: Callable[..., Any], globalns: Dict[Text, Any] | None = ..., localns: Dict[Text, Any] | None = ...
 ) -> None: ...
 @overload
 def cast(tp: Type[_T], obj: Any) -> _T: ...
diff --git a/stdlib/@python2/typing_extensions.pyi b/stdlib/@python2/typing_extensions.pyi
index 2499ae19d0f9..d946cc278d32 100644
--- a/stdlib/@python2/typing_extensions.pyi
+++ b/stdlib/@python2/typing_extensions.pyi
@@ -14,12 +14,10 @@ from typing import (
     Mapping,
     NewType as NewType,
     NoReturn as NoReturn,
-    Optional,
     Text as Text,
     Tuple,
     Type as Type,
     TypeVar,
-    Union,
     ValuesView,
     _Alias,
     overload as overload,
@@ -67,8 +65,8 @@ OrderedDict = _Alias()
 
 def get_type_hints(
     obj: Callable[..., Any],
-    globalns: Optional[Dict[str, Any]] = ...,
-    localns: Optional[Dict[str, Any]] = ...,
+    globalns: Dict[str, Any] | None = ...,
+    localns: Dict[str, Any] | None = ...,
     include_extras: bool = ...,
 ) -> Dict[str, Any]: ...
 
@@ -91,11 +89,11 @@ class ParamSpecKwargs:
 
 class ParamSpec:
     __name__: str
-    __bound__: Optional[Type[Any]]
+    __bound__: Type[Any] | None
     __covariant__: bool
     __contravariant__: bool
     def __init__(
-        self, name: str, *, bound: Union[None, Type[Any], str] = ..., contravariant: bool = ..., covariant: bool = ...
+        self, name: str, *, bound: None | Type[Any] | str = ..., contravariant: bool = ..., covariant: bool = ...
     ) -> None: ...
     @property
     def args(self) -> ParamSpecArgs: ...
diff --git a/stdlib/@python2/unicodedata.pyi b/stdlib/@python2/unicodedata.pyi
index 19c4a6781660..f4ca655e5c7e 100644
--- a/stdlib/@python2/unicodedata.pyi
+++ b/stdlib/@python2/unicodedata.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Text, TypeVar, Union
+from typing import Any, Text, TypeVar
 
 ucd_3_2_0: UCD
 ucnhash_CAPI: Any
@@ -9,15 +9,15 @@ _T = TypeVar("_T")
 def bidirectional(__chr: Text) -> Text: ...
 def category(__chr: Text) -> Text: ...
 def combining(__chr: Text) -> int: ...
-def decimal(__chr: Text, __default: _T = ...) -> Union[int, _T]: ...
+def decimal(__chr: Text, __default: _T = ...) -> int | _T: ...
 def decomposition(__chr: Text) -> Text: ...
-def digit(__chr: Text, __default: _T = ...) -> Union[int, _T]: ...
+def digit(__chr: Text, __default: _T = ...) -> int | _T: ...
 def east_asian_width(__chr: Text) -> Text: ...
-def lookup(__name: Union[Text, bytes]) -> Text: ...
+def lookup(__name: Text | bytes) -> Text: ...
 def mirrored(__chr: Text) -> int: ...
-def name(__chr: Text, __default: _T = ...) -> Union[Text, _T]: ...
+def name(__chr: Text, __default: _T = ...) -> Text | _T: ...
 def normalize(__form: Text, __unistr: Text) -> Text: ...
-def numeric(__chr: Text, __default: _T = ...) -> Union[float, _T]: ...
+def numeric(__chr: Text, __default: _T = ...) -> float | _T: ...
 
 class UCD(object):
     # The methods below are constructed from the same array in C
@@ -26,12 +26,12 @@ class UCD(object):
     def bidirectional(self, __chr: Text) -> str: ...
     def category(self, __chr: Text) -> str: ...
     def combining(self, __chr: Text) -> int: ...
-    def decimal(self, __chr: Text, __default: _T = ...) -> Union[int, _T]: ...
+    def decimal(self, __chr: Text, __default: _T = ...) -> int | _T: ...
     def decomposition(self, __chr: Text) -> str: ...
-    def digit(self, __chr: Text, __default: _T = ...) -> Union[int, _T]: ...
+    def digit(self, __chr: Text, __default: _T = ...) -> int | _T: ...
     def east_asian_width(self, __chr: Text) -> str: ...
-    def lookup(self, __name: Union[Text, bytes]) -> Text: ...
+    def lookup(self, __name: Text | bytes) -> Text: ...
     def mirrored(self, __chr: Text) -> int: ...
-    def name(self, __chr: Text, __default: _T = ...) -> Union[Text, _T]: ...
+    def name(self, __chr: Text, __default: _T = ...) -> Text | _T: ...
     def normalize(self, __form: Text, __unistr: Text) -> Text: ...
-    def numeric(self, __chr: Text, __default: _T = ...) -> Union[float, _T]: ...
+    def numeric(self, __chr: Text, __default: _T = ...) -> float | _T: ...
diff --git a/stdlib/@python2/unittest.pyi b/stdlib/@python2/unittest.pyi
index 57b73a762cfa..65a5a7878de6 100644
--- a/stdlib/@python2/unittest.pyi
+++ b/stdlib/@python2/unittest.pyi
@@ -11,7 +11,6 @@ from typing import (
     List,
     Mapping,
     NoReturn,
-    Optional,
     Pattern,
     Sequence,
     Set,
@@ -79,7 +78,7 @@ class _AssertRaisesContext(_AssertRaisesBaseContext):
 class TestCase(Testable):
     failureException: Type[BaseException]
     longMessage: bool
-    maxDiff: Optional[int]
+    maxDiff: int | None
     # undocumented
     _testMethodName: str
     def __init__(self, methodName: str = ...) -> None: ...
@@ -144,9 +143,7 @@ class TestCase(Testable):
     ) -> None: ...
     def assertListEqual(self, first: List[Any], second: List[Any], msg: object = ...) -> None: ...
     def assertTupleEqual(self, first: Tuple[Any, ...], second: Tuple[Any, ...], msg: object = ...) -> None: ...
-    def assertSetEqual(
-        self, first: Union[Set[Any], FrozenSet[Any]], second: Union[Set[Any], FrozenSet[Any]], msg: object = ...
-    ) -> None: ...
+    def assertSetEqual(self, first: Set[Any] | FrozenSet[Any], second: Set[Any] | FrozenSet[Any], msg: object = ...) -> None: ...
     def assertDictEqual(self, first: Dict[Any, Any], second: Dict[Any, Any], msg: object = ...) -> None: ...
     def assertLess(self, first: Any, second: Any, msg: object = ...) -> None: ...
     def assertLessEqual(self, first: Any, second: Any, msg: object = ...) -> None: ...
@@ -177,8 +174,8 @@ class TestCase(Testable):
     def assertIsNotNone(self, expr: Any, msg: object = ...) -> None: ...
     def assertIn(self, first: _T, second: Iterable[_T], msg: object = ...) -> None: ...
     def assertNotIn(self, first: _T, second: Iterable[_T], msg: object = ...) -> None: ...
-    def assertIsInstance(self, obj: Any, cls: Union[type, Tuple[type, ...]], msg: object = ...) -> None: ...
-    def assertNotIsInstance(self, obj: Any, cls: Union[type, Tuple[type, ...]], msg: object = ...) -> None: ...
+    def assertIsInstance(self, obj: Any, cls: type | Tuple[type, ...], msg: object = ...) -> None: ...
+    def assertNotIsInstance(self, obj: Any, cls: type | Tuple[type, ...], msg: object = ...) -> None: ...
     def fail(self, msg: object = ...) -> NoReturn: ...
     def countTestCases(self) -> int: ...
     def defaultTestResult(self) -> TestResult: ...
@@ -187,16 +184,16 @@ class TestCase(Testable):
     def addCleanup(self, function: Any, *args: Any, **kwargs: Any) -> None: ...
     def doCleanups(self) -> bool: ...
     def skipTest(self, reason: Any) -> None: ...
-    def _formatMessage(self, msg: Optional[Text], standardMsg: Text) -> str: ...  # undocumented
+    def _formatMessage(self, msg: Text | None, standardMsg: Text) -> str: ...  # undocumented
     def _getAssertEqualityFunc(self, first: Any, second: Any) -> Callable[..., None]: ...  # undocumented
 
 class FunctionTestCase(TestCase):
     def __init__(
         self,
         testFunc: Callable[[], None],
-        setUp: Optional[Callable[[], None]] = ...,
-        tearDown: Optional[Callable[[], None]] = ...,
-        description: Optional[str] = ...,
+        setUp: Callable[[], None] | None = ...,
+        tearDown: Callable[[], None] | None = ...,
+        description: str | None = ...,
     ) -> None: ...
     def debug(self) -> None: ...
     def countTestCases(self) -> int: ...
@@ -212,13 +209,13 @@ class TestSuite(Testable):
 
 class TestLoader:
     testMethodPrefix: str
-    sortTestMethodsUsing: Optional[Callable[[str, str], int]]
+    sortTestMethodsUsing: Callable[[str, str], int] | None
     suiteClass: Callable[[List[TestCase]], TestSuite]
     def loadTestsFromTestCase(self, testCaseClass: Type[TestCase]) -> TestSuite: ...
     def loadTestsFromModule(self, module: types.ModuleType = ..., use_load_tests: bool = ...) -> TestSuite: ...
-    def loadTestsFromName(self, name: str = ..., module: Optional[types.ModuleType] = ...) -> TestSuite: ...
-    def loadTestsFromNames(self, names: List[str] = ..., module: Optional[types.ModuleType] = ...) -> TestSuite: ...
-    def discover(self, start_dir: str, pattern: str = ..., top_level_dir: Optional[str] = ...) -> TestSuite: ...
+    def loadTestsFromName(self, name: str = ..., module: types.ModuleType | None = ...) -> TestSuite: ...
+    def loadTestsFromNames(self, names: List[str] = ..., module: types.ModuleType | None = ...) -> TestSuite: ...
+    def discover(self, start_dir: str, pattern: str = ..., top_level_dir: str | None = ...) -> TestSuite: ...
     def getTestCaseNames(self, testCaseClass: Type[TestCase] = ...) -> List[str]: ...
 
 defaultTestLoader: TestLoader
@@ -232,12 +229,12 @@ class TextTestResult(TestResult):
 class TextTestRunner:
     def __init__(
         self,
-        stream: Optional[TextIO] = ...,
+        stream: TextIO | None = ...,
         descriptions: bool = ...,
         verbosity: int = ...,
         failfast: bool = ...,
         buffer: bool = ...,
-        resultclass: Optional[Type[TestResult]] = ...,
+        resultclass: Type[TestResult] | None = ...,
     ) -> None: ...
     def _makeResult(self) -> TestResult: ...
     def run(self, test: Testable) -> TestResult: ...  # undocumented
@@ -245,10 +242,10 @@ class TextTestRunner:
 class SkipTest(Exception): ...
 
 # TODO precise types
-def skipUnless(condition: Any, reason: Union[str, unicode]) -> Any: ...
-def skipIf(condition: Any, reason: Union[str, unicode]) -> Any: ...
+def skipUnless(condition: Any, reason: str | unicode) -> Any: ...
+def skipIf(condition: Any, reason: str | unicode) -> Any: ...
 def expectedFailure(func: _FT) -> _FT: ...
-def skip(reason: Union[str, unicode]) -> Any: ...
+def skip(reason: str | unicode) -> Any: ...
 
 # not really documented
 class TestProgram:
@@ -256,18 +253,18 @@ class TestProgram:
     def runTests(self) -> None: ...  # undocumented
 
 def main(
-    module: Union[None, Text, types.ModuleType] = ...,
-    defaultTest: Optional[str] = ...,
-    argv: Optional[Sequence[str]] = ...,
-    testRunner: Union[Type[TextTestRunner], TextTestRunner, None] = ...,
+    module: None | Text | types.ModuleType = ...,
+    defaultTest: str | None = ...,
+    argv: Sequence[str] | None = ...,
+    testRunner: Type[TextTestRunner] | TextTestRunner | None = ...,
     testLoader: TestLoader = ...,
     exit: bool = ...,
     verbosity: int = ...,
-    failfast: Optional[bool] = ...,
-    catchbreak: Optional[bool] = ...,
-    buffer: Optional[bool] = ...,
+    failfast: bool | None = ...,
+    catchbreak: bool | None = ...,
+    buffer: bool | None = ...,
 ) -> TestProgram: ...
-def load_tests(loader: TestLoader, tests: TestSuite, pattern: Optional[Text]) -> TestSuite: ...
+def load_tests(loader: TestLoader, tests: TestSuite, pattern: Text | None) -> TestSuite: ...
 def installHandler() -> None: ...
 def registerResult(result: TestResult) -> None: ...
 def removeResult(result: TestResult) -> bool: ...
diff --git a/stdlib/@python2/urllib.pyi b/stdlib/@python2/urllib.pyi
index 30aaec8095b4..f6bb555b9581 100644
--- a/stdlib/@python2/urllib.pyi
+++ b/stdlib/@python2/urllib.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, AnyStr, List, Mapping, Sequence, Text, Tuple, TypeVar, Union
+from typing import IO, Any, AnyStr, List, Mapping, Sequence, Text, Tuple, TypeVar
 
 def url2pathname(pathname: AnyStr) -> AnyStr: ...
 def pathname2url(pathname: AnyStr) -> AnyStr: ...
@@ -125,7 +125,7 @@ def unquote(s: AnyStr) -> AnyStr: ...
 def unquote_plus(s: AnyStr) -> AnyStr: ...
 def quote(s: AnyStr, safe: Text = ...) -> AnyStr: ...
 def quote_plus(s: AnyStr, safe: Text = ...) -> AnyStr: ...
-def urlencode(query: Union[Sequence[Tuple[Any, Any]], Mapping[Any, Any]], doseq=...) -> str: ...
+def urlencode(query: Sequence[Tuple[Any, Any]] | Mapping[Any, Any], doseq=...) -> str: ...
 def getproxies() -> Mapping[str, str]: ...
 def proxy_bypass(host: str) -> Any: ...  # undocumented
 
diff --git a/stdlib/@python2/urllib2.pyi b/stdlib/@python2/urllib2.pyi
index 8c355db46d75..bf6157b8428b 100644
--- a/stdlib/@python2/urllib2.pyi
+++ b/stdlib/@python2/urllib2.pyi
@@ -1,12 +1,12 @@
 import ssl
 from httplib import HTTPConnectionProtocol, HTTPResponse
-from typing import Any, AnyStr, Callable, Dict, List, Mapping, Optional, Sequence, Text, Tuple, Type, Union
+from typing import Any, AnyStr, Callable, Dict, List, Mapping, Sequence, Text, Tuple, Type, Union
 from urllib import addinfourl
 
 _string = Union[str, unicode]
 
 class URLError(IOError):
-    reason: Union[str, BaseException]
+    reason: str | BaseException
 
 class HTTPError(URLError, addinfourl):
     code: int
@@ -19,16 +19,16 @@ class Request(object):
     data: str
     headers: Dict[str, str]
     unverifiable: bool
-    type: Optional[str]
+    type: str | None
     origin_req_host = ...
     unredirected_hdrs: Dict[str, str]
-    timeout: Optional[float]  # Undocumented, only set after __init__() by OpenerDirector.open()
+    timeout: float | None  # Undocumented, only set after __init__() by OpenerDirector.open()
     def __init__(
         self,
         url: str,
-        data: Optional[str] = ...,
+        data: str | None = ...,
         headers: Dict[str, str] = ...,
-        origin_req_host: Optional[str] = ...,
+        origin_req_host: str | None = ...,
         unverifiable: bool = ...,
     ) -> None: ...
     def __getattr__(self, attr): ...
@@ -47,30 +47,28 @@ class Request(object):
     def add_header(self, key: str, val: str) -> None: ...
     def add_unredirected_header(self, key: str, val: str) -> None: ...
     def has_header(self, header_name: str) -> bool: ...
-    def get_header(self, header_name: str, default: Optional[str] = ...) -> str: ...
+    def get_header(self, header_name: str, default: str | None = ...) -> str: ...
     def header_items(self): ...
 
 class OpenerDirector(object):
     addheaders: List[Tuple[str, str]]
     def add_handler(self, handler: BaseHandler) -> None: ...
-    def open(
-        self, fullurl: Union[Request, _string], data: Optional[_string] = ..., timeout: Optional[float] = ...
-    ) -> Optional[addinfourl]: ...
+    def open(self, fullurl: Request | _string, data: _string | None = ..., timeout: float | None = ...) -> addinfourl | None: ...
     def error(self, proto: _string, *args: Any): ...
 
 # Note that this type is somewhat a lie. The return *can* be None if
 # a custom opener has been installed that fails to handle the request.
 def urlopen(
-    url: Union[Request, _string],
-    data: Optional[_string] = ...,
-    timeout: Optional[float] = ...,
-    cafile: Optional[_string] = ...,
-    capath: Optional[_string] = ...,
+    url: Request | _string,
+    data: _string | None = ...,
+    timeout: float | None = ...,
+    cafile: _string | None = ...,
+    capath: _string | None = ...,
     cadefault: bool = ...,
-    context: Optional[ssl.SSLContext] = ...,
+    context: ssl.SSLContext | None = ...,
 ) -> addinfourl: ...
 def install_opener(opener: OpenerDirector) -> None: ...
-def build_opener(*handlers: Union[BaseHandler, Type[BaseHandler]]) -> OpenerDirector: ...
+def build_opener(*handlers: BaseHandler | Type[BaseHandler]) -> OpenerDirector: ...
 
 class BaseHandler:
     handler_order: int
@@ -97,21 +95,21 @@ class HTTPRedirectHandler(BaseHandler):
 
 class ProxyHandler(BaseHandler):
     proxies: Mapping[str, str]
-    def __init__(self, proxies: Optional[Mapping[str, str]] = ...): ...
+    def __init__(self, proxies: Mapping[str, str] | None = ...): ...
     def proxy_open(self, req: Request, proxy, type): ...
 
 class HTTPPasswordMgr:
     def __init__(self) -> None: ...
-    def add_password(self, realm: Optional[Text], uri: Union[Text, Sequence[Text]], user: Text, passwd: Text) -> None: ...
-    def find_user_password(self, realm: Optional[Text], authuri: Text) -> Tuple[Any, Any]: ...
+    def add_password(self, realm: Text | None, uri: Text | Sequence[Text], user: Text, passwd: Text) -> None: ...
+    def find_user_password(self, realm: Text | None, authuri: Text) -> Tuple[Any, Any]: ...
     def reduce_uri(self, uri: _string, default_port: bool = ...) -> Tuple[Any, Any]: ...
     def is_suburi(self, base: _string, test: _string) -> bool: ...
 
 class HTTPPasswordMgrWithDefaultRealm(HTTPPasswordMgr): ...
 
 class AbstractBasicAuthHandler:
-    def __init__(self, password_mgr: Optional[HTTPPasswordMgr] = ...) -> None: ...
-    def add_password(self, realm: Optional[Text], uri: Union[Text, Sequence[Text]], user: Text, passwd: Text) -> None: ...
+    def __init__(self, password_mgr: HTTPPasswordMgr | None = ...) -> None: ...
+    def add_password(self, realm: Text | None, uri: Text | Sequence[Text], user: Text, passwd: Text) -> None: ...
     def http_error_auth_reqed(self, authreq, host, req: Request, headers: Mapping[str, str]): ...
     def retry_http_basic_auth(self, host, req: Request, realm): ...
 
@@ -124,15 +122,15 @@ class ProxyBasicAuthHandler(AbstractBasicAuthHandler, BaseHandler):
     def http_error_407(self, req: Request, fp: addinfourl, code: int, msg: str, headers: Mapping[str, str]): ...
 
 class AbstractDigestAuthHandler:
-    def __init__(self, passwd: Optional[HTTPPasswordMgr] = ...) -> None: ...
-    def add_password(self, realm: Optional[Text], uri: Union[Text, Sequence[Text]], user: Text, passwd: Text) -> None: ...
+    def __init__(self, passwd: HTTPPasswordMgr | None = ...) -> None: ...
+    def add_password(self, realm: Text | None, uri: Text | Sequence[Text], user: Text, passwd: Text) -> None: ...
     def reset_retry_count(self) -> None: ...
     def http_error_auth_reqed(self, auth_header: str, host: str, req: Request, headers: Mapping[str, str]) -> None: ...
-    def retry_http_digest_auth(self, req: Request, auth: str) -> Optional[HTTPResponse]: ...
+    def retry_http_digest_auth(self, req: Request, auth: str) -> HTTPResponse | None: ...
     def get_cnonce(self, nonce: str) -> str: ...
     def get_authorization(self, req: Request, chal: Mapping[str, str]) -> str: ...
     def get_algorithm_impls(self, algorithm: str) -> Tuple[Callable[[str], str], Callable[[str, str], str]]: ...
-    def get_entity_digest(self, data: Optional[bytes], chal: Mapping[str, str]) -> Optional[str]: ...
+    def get_entity_digest(self, data: bytes | None, chal: Mapping[str, str]) -> str | None: ...
 
 class HTTPDigestAuthHandler(BaseHandler, AbstractDigestAuthHandler):
     auth_header: str
@@ -148,19 +146,19 @@ class AbstractHTTPHandler(BaseHandler):  # undocumented
     def __init__(self, debuglevel: int = ...) -> None: ...
     def set_http_debuglevel(self, level: int) -> None: ...
     def do_request_(self, request: Request) -> Request: ...
-    def do_open(self, http_class: HTTPConnectionProtocol, req: Request, **http_conn_args: Optional[Any]) -> addinfourl: ...
+    def do_open(self, http_class: HTTPConnectionProtocol, req: Request, **http_conn_args: Any | None) -> addinfourl: ...
 
 class HTTPHandler(AbstractHTTPHandler):
     def http_open(self, req: Request) -> addinfourl: ...
     def http_request(self, request: Request) -> Request: ...  # undocumented
 
 class HTTPSHandler(AbstractHTTPHandler):
-    def __init__(self, debuglevel: int = ..., context: Optional[ssl.SSLContext] = ...) -> None: ...
+    def __init__(self, debuglevel: int = ..., context: ssl.SSLContext | None = ...) -> None: ...
     def https_open(self, req: Request) -> addinfourl: ...
     def https_request(self, request: Request) -> Request: ...  # undocumented
 
 class HTTPCookieProcessor(BaseHandler):
-    def __init__(self, cookiejar: Optional[Any] = ...): ...
+    def __init__(self, cookiejar: Any | None = ...): ...
     def http_request(self, request: Request): ...
     def http_response(self, request: Request, response): ...
 
@@ -178,7 +176,7 @@ class FTPHandler(BaseHandler):
 
 class CacheFTPHandler(FTPHandler):
     def __init__(self) -> None: ...
-    def setTimeout(self, t: Optional[float]): ...
+    def setTimeout(self, t: float | None): ...
     def setMaxConns(self, m: int): ...
     def check_cache(self): ...
     def clear_cache(self): ...
diff --git a/stdlib/@python2/urlparse.pyi b/stdlib/@python2/urlparse.pyi
index 40691239a87b..6668c743373a 100644
--- a/stdlib/@python2/urlparse.pyi
+++ b/stdlib/@python2/urlparse.pyi
@@ -1,4 +1,4 @@
-from typing import AnyStr, Dict, List, NamedTuple, Optional, Sequence, Tuple, Union, overload
+from typing import AnyStr, Dict, List, NamedTuple, Sequence, Tuple, Union, overload
 
 _String = Union[str, unicode]
 
@@ -15,13 +15,13 @@ def clear_cache() -> None: ...
 
 class ResultMixin(object):
     @property
-    def username(self) -> Optional[str]: ...
+    def username(self) -> str | None: ...
     @property
-    def password(self) -> Optional[str]: ...
+    def password(self) -> str | None: ...
     @property
-    def hostname(self) -> Optional[str]: ...
+    def hostname(self) -> str | None: ...
     @property
-    def port(self) -> Optional[int]: ...
+    def port(self) -> int | None: ...
 
 class _SplitResult(NamedTuple):
     scheme: str
diff --git a/stdlib/@python2/uu.pyi b/stdlib/@python2/uu.pyi
index 69d5754bc216..e8717aecbe36 100644
--- a/stdlib/@python2/uu.pyi
+++ b/stdlib/@python2/uu.pyi
@@ -1,8 +1,8 @@
-from typing import BinaryIO, Optional, Text, Union
+from typing import BinaryIO, Text, Union
 
 _File = Union[Text, BinaryIO]
 
 class Error(Exception): ...
 
-def encode(in_file: _File, out_file: _File, name: Optional[str] = ..., mode: Optional[int] = ...) -> None: ...
-def decode(in_file: _File, out_file: Optional[_File] = ..., mode: Optional[int] = ..., quiet: int = ...) -> None: ...
+def encode(in_file: _File, out_file: _File, name: str | None = ..., mode: int | None = ...) -> None: ...
+def decode(in_file: _File, out_file: _File | None = ..., mode: int | None = ..., quiet: int = ...) -> None: ...
diff --git a/stdlib/@python2/uuid.pyi b/stdlib/@python2/uuid.pyi
index 791268a18475..2c8a9fb1c097 100644
--- a/stdlib/@python2/uuid.pyi
+++ b/stdlib/@python2/uuid.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Optional, Text, Tuple
+from typing import Any, Text, Tuple
 
 # Because UUID has properties called int and bytes we need to rename these temporarily.
 _Int = int
@@ -8,12 +8,12 @@ _FieldsType = Tuple[int, int, int, int, int, int]
 class UUID:
     def __init__(
         self,
-        hex: Optional[Text] = ...,
-        bytes: Optional[_Bytes] = ...,
-        bytes_le: Optional[_Bytes] = ...,
-        fields: Optional[_FieldsType] = ...,
-        int: Optional[_Int] = ...,
-        version: Optional[_Int] = ...,
+        hex: Text | None = ...,
+        bytes: _Bytes | None = ...,
+        bytes_le: _Bytes | None = ...,
+        fields: _FieldsType | None = ...,
+        int: _Int | None = ...,
+        version: _Int | None = ...,
     ) -> None: ...
     @property
     def bytes(self) -> _Bytes: ...
@@ -46,7 +46,7 @@ class UUID:
     @property
     def variant(self) -> str: ...
     @property
-    def version(self) -> Optional[_Int]: ...
+    def version(self) -> _Int | None: ...
     def __int__(self) -> _Int: ...
     def get_bytes(self) -> _Bytes: ...
     def get_bytes_le(self) -> _Bytes: ...
@@ -62,11 +62,11 @@ class UUID:
     def get_time_mid(self) -> _Int: ...
     def get_urn(self) -> str: ...
     def get_variant(self) -> str: ...
-    def get_version(self) -> Optional[_Int]: ...
+    def get_version(self) -> _Int | None: ...
     def __cmp__(self, other: Any) -> _Int: ...
 
 def getnode() -> int: ...
-def uuid1(node: Optional[_Int] = ..., clock_seq: Optional[_Int] = ...) -> UUID: ...
+def uuid1(node: _Int | None = ..., clock_seq: _Int | None = ...) -> UUID: ...
 def uuid3(namespace: UUID, name: str) -> UUID: ...
 def uuid4() -> UUID: ...
 def uuid5(namespace: UUID, name: str) -> UUID: ...
diff --git a/stdlib/@python2/warnings.pyi b/stdlib/@python2/warnings.pyi
index a94e9fc86d2e..e3540ed60b0c 100644
--- a/stdlib/@python2/warnings.pyi
+++ b/stdlib/@python2/warnings.pyi
@@ -1,20 +1,13 @@
 from types import ModuleType, TracebackType
-from typing import List, Optional, TextIO, Type, Union, overload
+from typing import List, TextIO, Type, overload
 from typing_extensions import Literal
 
 from _warnings import warn as warn, warn_explicit as warn_explicit
 
 def showwarning(
-    message: Union[Warning, str],
-    category: Type[Warning],
-    filename: str,
-    lineno: int,
-    file: Optional[TextIO] = ...,
-    line: Optional[str] = ...,
+    message: Warning | str, category: Type[Warning], filename: str, lineno: int, file: TextIO | None = ..., line: str | None = ...
 ) -> None: ...
-def formatwarning(
-    message: Union[Warning, str], category: Type[Warning], filename: str, lineno: int, line: Optional[str] = ...
-) -> str: ...
+def formatwarning(message: Warning | str, category: Type[Warning], filename: str, lineno: int, line: str | None = ...) -> str: ...
 def filterwarnings(
     action: str, message: str = ..., category: Type[Warning] = ..., module: str = ..., lineno: int = ..., append: bool = ...
 ) -> None: ...
@@ -24,32 +17,32 @@ def resetwarnings() -> None: ...
 class _OptionError(Exception): ...
 
 class WarningMessage:
-    message: Union[Warning, str]
+    message: Warning | str
     category: Type[Warning]
     filename: str
     lineno: int
-    file: Optional[TextIO]
-    line: Optional[str]
+    file: TextIO | None
+    line: str | None
     def __init__(
         self,
-        message: Union[Warning, str],
+        message: Warning | str,
         category: Type[Warning],
         filename: str,
         lineno: int,
-        file: Optional[TextIO] = ...,
-        line: Optional[str] = ...,
+        file: TextIO | None = ...,
+        line: str | None = ...,
     ) -> None: ...
 
 class catch_warnings:
     @overload
-    def __new__(cls, *, record: Literal[False] = ..., module: Optional[ModuleType] = ...) -> _catch_warnings_without_records: ...
+    def __new__(cls, *, record: Literal[False] = ..., module: ModuleType | None = ...) -> _catch_warnings_without_records: ...
     @overload
-    def __new__(cls, *, record: Literal[True], module: Optional[ModuleType] = ...) -> _catch_warnings_with_records: ...
+    def __new__(cls, *, record: Literal[True], module: ModuleType | None = ...) -> _catch_warnings_with_records: ...
     @overload
-    def __new__(cls, *, record: bool, module: Optional[ModuleType] = ...) -> catch_warnings: ...
-    def __enter__(self) -> Optional[List[WarningMessage]]: ...
+    def __new__(cls, *, record: bool, module: ModuleType | None = ...) -> catch_warnings: ...
+    def __enter__(self) -> List[WarningMessage] | None: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
 
 class _catch_warnings_without_records(catch_warnings):
diff --git a/stdlib/@python2/wave.pyi b/stdlib/@python2/wave.pyi
index 8615d8fad8ca..0e9fe612cd24 100644
--- a/stdlib/@python2/wave.pyi
+++ b/stdlib/@python2/wave.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, BinaryIO, NoReturn, Optional, Text, Tuple, Union
+from typing import IO, Any, BinaryIO, NoReturn, Text, Tuple, Union
 
 _File = Union[Text, IO[bytes]]
 
@@ -10,7 +10,7 @@ _wave_params = Tuple[int, int, int, int, str, str]
 
 class Wave_read:
     def __init__(self, f: _File) -> None: ...
-    def getfp(self) -> Optional[BinaryIO]: ...
+    def getfp(self) -> BinaryIO | None: ...
     def rewind(self) -> None: ...
     def close(self) -> None: ...
     def tell(self) -> int: ...
@@ -51,6 +51,6 @@ class Wave_write:
     def close(self) -> None: ...
 
 # Returns a Wave_read if mode is rb and Wave_write if mode is wb
-def open(f: _File, mode: Optional[str] = ...) -> Any: ...
+def open(f: _File, mode: str | None = ...) -> Any: ...
 
 openfp = open
diff --git a/stdlib/@python2/weakref.pyi b/stdlib/@python2/weakref.pyi
index 5e8f4cd12b03..6467f3a7517f 100644
--- a/stdlib/@python2/weakref.pyi
+++ b/stdlib/@python2/weakref.pyi
@@ -1,19 +1,5 @@
 from _weakrefset import WeakSet as WeakSet
-from typing import (
-    Any,
-    Callable,
-    Generic,
-    Iterable,
-    Iterator,
-    List,
-    Mapping,
-    MutableMapping,
-    Tuple,
-    Type,
-    TypeVar,
-    Union,
-    overload,
-)
+from typing import Any, Callable, Generic, Iterable, Iterator, List, Mapping, MutableMapping, Tuple, Type, TypeVar, overload
 
 from _weakref import (
     CallableProxyType as CallableProxyType,
@@ -37,7 +23,7 @@ class WeakValueDictionary(MutableMapping[_KT, _VT]):
     @overload
     def __init__(self) -> None: ...
     @overload
-    def __init__(self, __other: Union[Mapping[_KT, _VT], Iterable[Tuple[_KT, _VT]]], **kwargs: _VT) -> None: ...
+    def __init__(self, __other: Mapping[_KT, _VT] | Iterable[Tuple[_KT, _VT]], **kwargs: _VT) -> None: ...
     def __len__(self) -> int: ...
     def __getitem__(self, k: _KT) -> _VT: ...
     def __setitem__(self, k: _KT, v: _VT) -> None: ...
@@ -66,7 +52,7 @@ class WeakKeyDictionary(MutableMapping[_KT, _VT]):
     @overload
     def __init__(self, dict: None = ...) -> None: ...
     @overload
-    def __init__(self, dict: Union[Mapping[_KT, _VT], Iterable[Tuple[_KT, _VT]]]) -> None: ...
+    def __init__(self, dict: Mapping[_KT, _VT] | Iterable[Tuple[_KT, _VT]]) -> None: ...
     def __len__(self) -> int: ...
     def __getitem__(self, k: _KT) -> _VT: ...
     def __setitem__(self, k: _KT, v: _VT) -> None: ...
diff --git a/stdlib/@python2/webbrowser.pyi b/stdlib/@python2/webbrowser.pyi
index 9e143bb8c88f..f634bc11ca7d 100644
--- a/stdlib/@python2/webbrowser.pyi
+++ b/stdlib/@python2/webbrowser.pyi
@@ -1,12 +1,12 @@
 import sys
-from typing import Callable, List, Optional, Sequence, Text, Union
+from typing import Callable, List, Sequence, Text
 
 class Error(Exception): ...
 
 def register(
-    name: Text, klass: Optional[Callable[[], BaseBrowser]], instance: Optional[BaseBrowser] = ..., update_tryorder: int = ...
+    name: Text, klass: Callable[[], BaseBrowser] | None, instance: BaseBrowser | None = ..., update_tryorder: int = ...
 ) -> None: ...
-def get(using: Optional[Text] = ...) -> BaseBrowser: ...
+def get(using: Text | None = ...) -> BaseBrowser: ...
 def open(url: Text, new: int = ..., autoraise: bool = ...) -> bool: ...
 def open_new(url: Text) -> bool: ...
 def open_new_tab(url: Text) -> bool: ...
@@ -24,14 +24,14 @@ class GenericBrowser(BaseBrowser):
     args: List[str]
     name: str
     basename: str
-    def __init__(self, name: Union[Text, Sequence[Text]]) -> None: ...
+    def __init__(self, name: Text | Sequence[Text]) -> None: ...
     def open(self, url: Text, new: int = ..., autoraise: bool = ...) -> bool: ...
 
 class BackgroundBrowser(GenericBrowser):
     def open(self, url: Text, new: int = ..., autoraise: bool = ...) -> bool: ...
 
 class UnixBrowser(BaseBrowser):
-    raise_opts: Optional[List[str]]
+    raise_opts: List[str] | None
     background: bool
     redirect_stdout: bool
     remote_args: List[str]
diff --git a/stdlib/@python2/whichdb.pyi b/stdlib/@python2/whichdb.pyi
index 67542096d712..1c678e9392e8 100644
--- a/stdlib/@python2/whichdb.pyi
+++ b/stdlib/@python2/whichdb.pyi
@@ -1,3 +1,3 @@
-from typing import Optional, Text
+from typing import Text
 
-def whichdb(filename: Text) -> Optional[str]: ...
+def whichdb(filename: Text) -> str | None: ...
diff --git a/stdlib/@python2/winsound.pyi b/stdlib/@python2/winsound.pyi
index be9a8c660781..3d79f3b043f2 100644
--- a/stdlib/@python2/winsound.pyi
+++ b/stdlib/@python2/winsound.pyi
@@ -1,5 +1,5 @@
 import sys
-from typing import Optional, Union, overload
+from typing import overload
 from typing_extensions import Literal
 
 if sys.platform == "win32":
@@ -21,7 +21,7 @@ if sys.platform == "win32":
     def Beep(frequency: int, duration: int) -> None: ...
     # Can actually accept anything ORed with 4, and if not it's definitely str, but that's inexpressible
     @overload
-    def PlaySound(sound: Optional[bytes], flags: Literal[4]) -> None: ...
+    def PlaySound(sound: bytes | None, flags: Literal[4]) -> None: ...
     @overload
-    def PlaySound(sound: Optional[Union[str, bytes]], flags: int) -> None: ...
+    def PlaySound(sound: str | bytes | None, flags: int) -> None: ...
     def MessageBeep(type: int = ...) -> None: ...
diff --git a/stdlib/@python2/wsgiref/handlers.pyi b/stdlib/@python2/wsgiref/handlers.pyi
index e8d32bea3f7b..d7e35ba8aff6 100644
--- a/stdlib/@python2/wsgiref/handlers.pyi
+++ b/stdlib/@python2/wsgiref/handlers.pyi
@@ -8,7 +8,7 @@ from .util import FileWrapper
 
 _exc_info = Tuple[Optional[Type[BaseException]], Optional[BaseException], Optional[TracebackType]]
 
-def format_date_time(timestamp: Optional[float]) -> str: ...  # undocumented
+def format_date_time(timestamp: float | None) -> str: ...  # undocumented
 
 class BaseHandler:
     wsgi_version: Tuple[int, int]  # undocumented
@@ -18,14 +18,14 @@ class BaseHandler:
 
     origin_server: bool
     http_version: str
-    server_software: Optional[str]
+    server_software: str | None
 
     os_environ: MutableMapping[str, str]
 
-    wsgi_file_wrapper: Optional[Type[FileWrapper]]
+    wsgi_file_wrapper: Type[FileWrapper] | None
     headers_class: Type[Headers]  # undocumented
 
-    traceback_limit: Optional[int]
+    traceback_limit: int | None
     error_status: str
     error_headers: List[Tuple[Text, Text]]
     error_body: bytes
@@ -36,7 +36,7 @@ class BaseHandler:
     def set_content_length(self) -> None: ...
     def cleanup_headers(self) -> None: ...
     def start_response(
-        self, status: Text, headers: List[Tuple[Text, Text]], exc_info: Optional[_exc_info] = ...
+        self, status: Text, headers: List[Tuple[Text, Text]], exc_info: _exc_info | None = ...
     ) -> Callable[[bytes], None]: ...
     def send_preamble(self) -> None: ...
     def write(self, data: bytes) -> None: ...
diff --git a/stdlib/@python2/wsgiref/headers.pyi b/stdlib/@python2/wsgiref/headers.pyi
index b1c0d4f56fe6..08061fee7664 100644
--- a/stdlib/@python2/wsgiref/headers.pyi
+++ b/stdlib/@python2/wsgiref/headers.pyi
@@ -1,4 +1,4 @@
-from typing import List, Optional, Pattern, Tuple, overload
+from typing import List, Pattern, Tuple, overload
 
 _HeaderList = List[Tuple[str, str]]
 
@@ -9,16 +9,16 @@ class Headers:
     def __len__(self) -> int: ...
     def __setitem__(self, name: str, val: str) -> None: ...
     def __delitem__(self, name: str) -> None: ...
-    def __getitem__(self, name: str) -> Optional[str]: ...
+    def __getitem__(self, name: str) -> str | None: ...
     def has_key(self, name: str) -> bool: ...
     def __contains__(self, name: str) -> bool: ...
     def get_all(self, name: str) -> List[str]: ...
     @overload
     def get(self, name: str, default: str) -> str: ...
     @overload
-    def get(self, name: str, default: Optional[str] = ...) -> Optional[str]: ...
+    def get(self, name: str, default: str | None = ...) -> str | None: ...
     def keys(self) -> List[str]: ...
     def values(self) -> List[str]: ...
     def items(self) -> _HeaderList: ...
     def setdefault(self, name: str, value: str) -> str: ...
-    def add_header(self, _name: str, _value: Optional[str], **_params: Optional[str]) -> None: ...
+    def add_header(self, _name: str, _value: str | None, **_params: str | None) -> None: ...
diff --git a/stdlib/@python2/wsgiref/simple_server.pyi b/stdlib/@python2/wsgiref/simple_server.pyi
index 7e18442f6055..a74a26fed935 100644
--- a/stdlib/@python2/wsgiref/simple_server.pyi
+++ b/stdlib/@python2/wsgiref/simple_server.pyi
@@ -1,5 +1,5 @@
 from BaseHTTPServer import BaseHTTPRequestHandler, HTTPServer
-from typing import List, Optional, Type, TypeVar, overload
+from typing import List, Type, TypeVar, overload
 
 from .handlers import SimpleHandler
 from .types import ErrorStream, StartResponse, WSGIApplication, WSGIEnvironment
@@ -13,11 +13,11 @@ class ServerHandler(SimpleHandler):  # undocumented
     def close(self) -> None: ...
 
 class WSGIServer(HTTPServer):
-    application: Optional[WSGIApplication]
+    application: WSGIApplication | None
     base_environ: WSGIEnvironment  # only available after call to setup_environ()
     def setup_environ(self) -> None: ...
-    def get_app(self) -> Optional[WSGIApplication]: ...
-    def set_app(self, application: Optional[WSGIApplication]) -> None: ...
+    def get_app(self) -> WSGIApplication | None: ...
+    def set_app(self, application: WSGIApplication | None) -> None: ...
 
 class WSGIRequestHandler(BaseHTTPRequestHandler):
     server_version: str
diff --git a/stdlib/@python2/wsgiref/util.pyi b/stdlib/@python2/wsgiref/util.pyi
index e1179ebab365..c8e045a8cb8e 100644
--- a/stdlib/@python2/wsgiref/util.pyi
+++ b/stdlib/@python2/wsgiref/util.pyi
@@ -1,4 +1,4 @@
-from typing import IO, Any, Callable, Optional
+from typing import IO, Any, Callable
 
 from .types import WSGIEnvironment
 
@@ -14,6 +14,6 @@ class FileWrapper:
 def guess_scheme(environ: WSGIEnvironment) -> str: ...
 def application_uri(environ: WSGIEnvironment) -> str: ...
 def request_uri(environ: WSGIEnvironment, include_query: bool = ...) -> str: ...
-def shift_path_info(environ: WSGIEnvironment) -> Optional[str]: ...
+def shift_path_info(environ: WSGIEnvironment) -> str | None: ...
 def setup_testing_defaults(environ: WSGIEnvironment) -> None: ...
 def is_hop_by_hop(header_name: str) -> bool: ...
diff --git a/stdlib/@python2/wsgiref/validate.pyi b/stdlib/@python2/wsgiref/validate.pyi
index 5918374d5fd8..b3e629b02d71 100644
--- a/stdlib/@python2/wsgiref/validate.pyi
+++ b/stdlib/@python2/wsgiref/validate.pyi
@@ -1,5 +1,5 @@
 from _typeshed.wsgi import ErrorStream, InputStream, WSGIApplication
-from typing import Any, Callable, Iterable, Iterator, NoReturn, Optional
+from typing import Any, Callable, Iterable, Iterator, NoReturn
 
 class WSGIWarning(Warning): ...
 
@@ -36,8 +36,8 @@ class IteratorWrapper:
     original_iterator: Iterator[bytes]
     iterator: Iterator[bytes]
     closed: bool
-    check_start_response: Optional[bool]
-    def __init__(self, wsgi_iterator: Iterator[bytes], check_start_response: Optional[bool]) -> None: ...
+    check_start_response: bool | None
+    def __init__(self, wsgi_iterator: Iterator[bytes], check_start_response: bool | None) -> None: ...
     def __iter__(self) -> IteratorWrapper: ...
     def next(self) -> bytes: ...
     def close(self) -> None: ...
diff --git a/stdlib/@python2/xml/dom/domreg.pyi b/stdlib/@python2/xml/dom/domreg.pyi
index bf63ff09e106..2496b3884ea1 100644
--- a/stdlib/@python2/xml/dom/domreg.pyi
+++ b/stdlib/@python2/xml/dom/domreg.pyi
@@ -1,10 +1,8 @@
 from _typeshed.xml import DOMImplementation
-from typing import Callable, Dict, Iterable, Optional, Tuple, Union
+from typing import Callable, Dict, Iterable, Tuple
 
 well_known_implementations: Dict[str, str]
 registered: Dict[str, Callable[[], DOMImplementation]]
 
 def registerDOMImplementation(name: str, factory: Callable[[], DOMImplementation]) -> None: ...
-def getDOMImplementation(
-    name: Optional[str] = ..., features: Union[str, Iterable[Tuple[str, Optional[str]]]] = ...
-) -> DOMImplementation: ...
+def getDOMImplementation(name: str | None = ..., features: str | Iterable[Tuple[str, str | None]] = ...) -> DOMImplementation: ...
diff --git a/stdlib/@python2/xml/dom/minicompat.pyi b/stdlib/@python2/xml/dom/minicompat.pyi
index aa8efd03b19f..e9b0395ab50d 100644
--- a/stdlib/@python2/xml/dom/minicompat.pyi
+++ b/stdlib/@python2/xml/dom/minicompat.pyi
@@ -1,4 +1,4 @@
-from typing import Any, Iterable, List, Optional, Tuple, Type, TypeVar
+from typing import Any, Iterable, List, Tuple, Type, TypeVar
 
 _T = TypeVar("_T")
 
@@ -6,7 +6,7 @@ StringTypes: Tuple[Type[str]]
 
 class NodeList(List[_T]):
     length: int
-    def item(self, index: int) -> Optional[_T]: ...
+    def item(self, index: int) -> _T | None: ...
 
 class EmptyNodeList(Tuple[Any, ...]):
     length: int
diff --git a/stdlib/@python2/xml/dom/minidom.pyi b/stdlib/@python2/xml/dom/minidom.pyi
index 2f5988bf76e0..ed46ac4561ec 100644
--- a/stdlib/@python2/xml/dom/minidom.pyi
+++ b/stdlib/@python2/xml/dom/minidom.pyi
@@ -1,23 +1,23 @@
 import xml.dom
-from typing import IO, Any, Optional, Text as _Text, TypeVar, Union
+from typing import IO, Any, Text as _Text, TypeVar
 from xml.dom.xmlbuilder import DocumentLS, DOMImplementationLS
 from xml.sax.xmlreader import XMLReader
 
 _T = TypeVar("_T")
 
-def parse(file: Union[str, IO[Any]], parser: Optional[XMLReader] = ..., bufsize: Optional[int] = ...): ...
-def parseString(string: Union[bytes, _Text], parser: Optional[XMLReader] = ...): ...
+def parse(file: str | IO[Any], parser: XMLReader | None = ..., bufsize: int | None = ...): ...
+def parseString(string: bytes | _Text, parser: XMLReader | None = ...): ...
 def getDOMImplementation(features=...): ...
 
 class Node(xml.dom.Node):
-    namespaceURI: Optional[str]
+    namespaceURI: str | None
     parentNode: Any
     ownerDocument: Any
     nextSibling: Any
     previousSibling: Any
     prefix: Any
-    def toxml(self, encoding: Optional[Any] = ...): ...
-    def toprettyxml(self, indent: str = ..., newl: str = ..., encoding: Optional[Any] = ...): ...
+    def toxml(self, encoding: Any | None = ...): ...
+    def toprettyxml(self, indent: str = ..., newl: str = ..., encoding: Any | None = ...): ...
     def hasChildNodes(self) -> bool: ...
     def insertBefore(self, newChild, refChild): ...
     def appendChild(self, node): ...
@@ -50,14 +50,14 @@ class Attr(Node):
     attributes: Any
     specified: bool
     ownerElement: Any
-    namespaceURI: Optional[str]
+    namespaceURI: str | None
     childNodes: Any
     nodeName: Any
     nodeValue: str
     value: str
     prefix: Any
     def __init__(
-        self, qName: str, namespaceURI: Optional[str] = ..., localName: Optional[Any] = ..., prefix: Optional[Any] = ...
+        self, qName: str, namespaceURI: str | None = ..., localName: Any | None = ..., prefix: Any | None = ...
     ) -> None: ...
     def unlink(self) -> None: ...
 
@@ -70,7 +70,7 @@ class NamedNodeMap:
     def keys(self): ...
     def keysNS(self): ...
     def values(self): ...
-    def get(self, name, value: Optional[Any] = ...): ...
+    def get(self, name, value: Any | None = ...): ...
     def __len__(self) -> int: ...
     def __eq__(self, other: Any) -> bool: ...
     def __ge__(self, other: Any) -> bool: ...
@@ -101,11 +101,11 @@ class Element(Node):
     parentNode: Any
     tagName: str
     prefix: Any
-    namespaceURI: Optional[str]
+    namespaceURI: str | None
     childNodes: Any
     nextSibling: Any
     def __init__(
-        self, tagName, namespaceURI: Optional[str] = ..., prefix: Optional[Any] = ..., localName: Optional[Any] = ...
+        self, tagName, namespaceURI: str | None = ..., prefix: Any | None = ..., localName: Any | None = ...
     ) -> None: ...
     def unlink(self) -> None: ...
     def getAttribute(self, attname): ...
@@ -288,7 +288,5 @@ class Document(Node, DocumentLS):
     def getElementsByTagNameNS(self, namespaceURI: str, localName): ...
     def isSupported(self, feature, version): ...
     def importNode(self, node, deep): ...
-    def writexml(
-        self, writer, indent: str = ..., addindent: str = ..., newl: str = ..., encoding: Optional[Any] = ...
-    ) -> None: ...
+    def writexml(self, writer, indent: str = ..., addindent: str = ..., newl: str = ..., encoding: Any | None = ...) -> None: ...
     def renameNode(self, n, namespaceURI: str, name): ...
diff --git a/stdlib/@python2/xml/etree/ElementInclude.pyi b/stdlib/@python2/xml/etree/ElementInclude.pyi
index c6144e40852a..b74285d3e9b7 100644
--- a/stdlib/@python2/xml/etree/ElementInclude.pyi
+++ b/stdlib/@python2/xml/etree/ElementInclude.pyi
@@ -1,4 +1,4 @@
-from typing import Callable, Optional, Union
+from typing import Callable
 from xml.etree.ElementTree import Element
 
 XINCLUDE: str
@@ -7,9 +7,9 @@ XINCLUDE_FALLBACK: str
 
 class FatalIncludeError(SyntaxError): ...
 
-def default_loader(href: Union[str, bytes, int], parse: str, encoding: Optional[str] = ...) -> Union[str, Element]: ...
+def default_loader(href: str | bytes | int, parse: str, encoding: str | None = ...) -> str | Element: ...
 
 # TODO: loader is of type default_loader ie it takes a callable that has the
 # same signature as default_loader. But default_loader has a keyword argument
 # Which can't be represented using Callable...
-def include(elem: Element, loader: Optional[Callable[..., Union[str, Element]]] = ...) -> None: ...
+def include(elem: Element, loader: Callable[..., str | Element] | None = ...) -> None: ...
diff --git a/stdlib/@python2/xml/etree/ElementPath.pyi b/stdlib/@python2/xml/etree/ElementPath.pyi
index de49ffcf1209..02fe84567543 100644
--- a/stdlib/@python2/xml/etree/ElementPath.pyi
+++ b/stdlib/@python2/xml/etree/ElementPath.pyi
@@ -1,4 +1,4 @@
-from typing import Callable, Dict, Generator, List, Optional, Pattern, Tuple, TypeVar, Union
+from typing import Callable, Dict, Generator, List, Pattern, Tuple, TypeVar
 from xml.etree.ElementTree import Element
 
 xpath_tokenizer_re: Pattern[str]
@@ -7,7 +7,7 @@ _token = Tuple[str, str]
 _next = Callable[[], _token]
 _callback = Callable[[_SelectorContext, List[Element]], Generator[Element, None, None]]
 
-def xpath_tokenizer(pattern: str, namespaces: Optional[Dict[str, str]] = ...) -> Generator[_token, None, None]: ...
+def xpath_tokenizer(pattern: str, namespaces: Dict[str, str] | None = ...) -> Generator[_token, None, None]: ...
 def get_parent_map(context: _SelectorContext) -> Dict[Element, Element]: ...
 def prepare_child(next: _next, token: _token) -> _callback: ...
 def prepare_star(next: _next, token: _token) -> _callback: ...
@@ -19,15 +19,13 @@ def prepare_predicate(next: _next, token: _token) -> _callback: ...
 ops: Dict[str, Callable[[_next, _token], _callback]]
 
 class _SelectorContext:
-    parent_map: Optional[Dict[Element, Element]]
+    parent_map: Dict[Element, Element] | None
     root: Element
     def __init__(self, root: Element) -> None: ...
 
 _T = TypeVar("_T")
 
-def iterfind(elem: Element, path: str, namespaces: Optional[Dict[str, str]] = ...) -> Generator[Element, None, None]: ...
-def find(elem: Element, path: str, namespaces: Optional[Dict[str, str]] = ...) -> Optional[Element]: ...
-def findall(elem: Element, path: str, namespaces: Optional[Dict[str, str]] = ...) -> List[Element]: ...
-def findtext(
-    elem: Element, path: str, default: Optional[_T] = ..., namespaces: Optional[Dict[str, str]] = ...
-) -> Union[_T, str]: ...
+def iterfind(elem: Element, path: str, namespaces: Dict[str, str] | None = ...) -> Generator[Element, None, None]: ...
+def find(elem: Element, path: str, namespaces: Dict[str, str] | None = ...) -> Element | None: ...
+def findall(elem: Element, path: str, namespaces: Dict[str, str] | None = ...) -> List[Element]: ...
+def findtext(elem: Element, path: str, default: _T | None = ..., namespaces: Dict[str, str] | None = ...) -> _T | str: ...
diff --git a/stdlib/@python2/xml/etree/ElementTree.pyi b/stdlib/@python2/xml/etree/ElementTree.pyi
index f7527fa5d890..a7a0a1c65f46 100644
--- a/stdlib/@python2/xml/etree/ElementTree.pyi
+++ b/stdlib/@python2/xml/etree/ElementTree.pyi
@@ -11,7 +11,6 @@ from typing import (
     KeysView,
     List,
     MutableSequence,
-    Optional,
     Sequence,
     Text,
     Tuple,
@@ -55,11 +54,11 @@ _file_or_filename = Union[Text, FileDescriptor, IO[Any]]
 class Element(MutableSequence[Element]):
     tag: _str_result_type
     attrib: Dict[_str_result_type, _str_result_type]
-    text: Optional[_str_result_type]
-    tail: Optional[_str_result_type]
+    text: _str_result_type | None
+    tail: _str_result_type | None
     def __init__(
         self,
-        tag: Union[_str_argument_type, Callable[..., Element]],
+        tag: _str_argument_type | Callable[..., Element],
         attrib: Dict[_str_argument_type, _str_argument_type] = ...,
         **extra: _str_argument_type,
     ) -> None: ...
@@ -67,38 +66,35 @@ class Element(MutableSequence[Element]):
     def clear(self) -> None: ...
     def extend(self, __elements: Iterable[Element]) -> None: ...
     def find(
-        self, path: _str_argument_type, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
-    ) -> Optional[Element]: ...
+        self, path: _str_argument_type, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
+    ) -> Element | None: ...
     def findall(
-        self, path: _str_argument_type, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
+        self, path: _str_argument_type, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
     ) -> List[Element]: ...
     @overload
     def findtext(
-        self,
-        path: _str_argument_type,
-        default: None = ...,
-        namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...,
-    ) -> Optional[_str_result_type]: ...
+        self, path: _str_argument_type, default: None = ..., namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
+    ) -> _str_result_type | None: ...
     @overload
     def findtext(
-        self, path: _str_argument_type, default: _T, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
-    ) -> Union[_T, _str_result_type]: ...
+        self, path: _str_argument_type, default: _T, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
+    ) -> _T | _str_result_type: ...
     @overload
-    def get(self, key: _str_argument_type, default: None = ...) -> Optional[_str_result_type]: ...
+    def get(self, key: _str_argument_type, default: None = ...) -> _str_result_type | None: ...
     @overload
-    def get(self, key: _str_argument_type, default: _T) -> Union[_str_result_type, _T]: ...
+    def get(self, key: _str_argument_type, default: _T) -> _str_result_type | _T: ...
     def insert(self, __index: int, __element: Element) -> None: ...
     def items(self) -> ItemsView[_str_result_type, _str_result_type]: ...
-    def iter(self, tag: Optional[_str_argument_type] = ...) -> Generator[Element, None, None]: ...
+    def iter(self, tag: _str_argument_type | None = ...) -> Generator[Element, None, None]: ...
     def iterfind(
-        self, path: _str_argument_type, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
+        self, path: _str_argument_type, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
     ) -> Generator[Element, None, None]: ...
     def itertext(self) -> Generator[_str_result_type, None, None]: ...
     def keys(self) -> KeysView[_str_result_type]: ...
     def makeelement(self, __tag: _str_argument_type, __attrib: Dict[_str_argument_type, _str_argument_type]) -> Element: ...
     def remove(self, __subelement: Element) -> None: ...
     def set(self, __key: _str_argument_type, __value: _str_argument_type) -> None: ...
-    def __delitem__(self, i: Union[int, slice]) -> None: ...
+    def __delitem__(self, i: int | slice) -> None: ...
     @overload
     def __getitem__(self, i: int) -> Element: ...
     @overload
@@ -109,7 +105,7 @@ class Element(MutableSequence[Element]):
     @overload
     def __setitem__(self, s: slice, o: Iterable[Element]) -> None: ...
     def getchildren(self) -> List[Element]: ...
-    def getiterator(self, tag: Optional[_str_argument_type] = ...) -> List[Element]: ...
+    def getiterator(self, tag: _str_argument_type | None = ...) -> List[Element]: ...
 
 def SubElement(
     parent: Element,
@@ -117,66 +113,63 @@ def SubElement(
     attrib: Dict[_str_argument_type, _str_argument_type] = ...,
     **extra: _str_argument_type,
 ) -> Element: ...
-def Comment(text: Optional[_str_argument_type] = ...) -> Element: ...
-def ProcessingInstruction(target: _str_argument_type, text: Optional[_str_argument_type] = ...) -> Element: ...
+def Comment(text: _str_argument_type | None = ...) -> Element: ...
+def ProcessingInstruction(target: _str_argument_type, text: _str_argument_type | None = ...) -> Element: ...
 
 PI: Callable[..., Element]
 
 class QName:
     text: str
-    def __init__(self, text_or_uri: _str_argument_type, tag: Optional[_str_argument_type] = ...) -> None: ...
+    def __init__(self, text_or_uri: _str_argument_type, tag: _str_argument_type | None = ...) -> None: ...
 
 class ElementTree:
-    def __init__(self, element: Optional[Element] = ..., file: Optional[_file_or_filename] = ...) -> None: ...
+    def __init__(self, element: Element | None = ..., file: _file_or_filename | None = ...) -> None: ...
     def getroot(self) -> Element: ...
-    def parse(self, source: _file_or_filename, parser: Optional[XMLParser] = ...) -> Element: ...
-    def iter(self, tag: Optional[_str_argument_type] = ...) -> Generator[Element, None, None]: ...
-    def getiterator(self, tag: Optional[_str_argument_type] = ...) -> List[Element]: ...
+    def parse(self, source: _file_or_filename, parser: XMLParser | None = ...) -> Element: ...
+    def iter(self, tag: _str_argument_type | None = ...) -> Generator[Element, None, None]: ...
+    def getiterator(self, tag: _str_argument_type | None = ...) -> List[Element]: ...
     def find(
-        self, path: _str_argument_type, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
-    ) -> Optional[Element]: ...
+        self, path: _str_argument_type, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
+    ) -> Element | None: ...
     @overload
     def findtext(
-        self,
-        path: _str_argument_type,
-        default: None = ...,
-        namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...,
-    ) -> Optional[_str_result_type]: ...
+        self, path: _str_argument_type, default: None = ..., namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
+    ) -> _str_result_type | None: ...
     @overload
     def findtext(
-        self, path: _str_argument_type, default: _T, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
-    ) -> Union[_T, _str_result_type]: ...
+        self, path: _str_argument_type, default: _T, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
+    ) -> _T | _str_result_type: ...
     def findall(
-        self, path: _str_argument_type, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
+        self, path: _str_argument_type, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
     ) -> List[Element]: ...
     def iterfind(
-        self, path: _str_argument_type, namespaces: Optional[Dict[_str_argument_type, _str_argument_type]] = ...
+        self, path: _str_argument_type, namespaces: Dict[_str_argument_type, _str_argument_type] | None = ...
     ) -> Generator[Element, None, None]: ...
     def write(
         self,
         file_or_filename: _file_or_filename,
-        encoding: Optional[str] = ...,
-        xml_declaration: Optional[bool] = ...,
-        default_namespace: Optional[_str_argument_type] = ...,
-        method: Optional[str] = ...,
+        encoding: str | None = ...,
+        xml_declaration: bool | None = ...,
+        default_namespace: _str_argument_type | None = ...,
+        method: str | None = ...,
     ) -> None: ...
     def write_c14n(self, file: _file_or_filename) -> None: ...
 
 def register_namespace(prefix: _str_argument_type, uri: _str_argument_type) -> None: ...
-def tostring(element: Element, encoding: Optional[str] = ..., method: Optional[str] = ...) -> bytes: ...
-def tostringlist(element: Element, encoding: Optional[str] = ..., method: Optional[str] = ...) -> List[bytes]: ...
+def tostring(element: Element, encoding: str | None = ..., method: str | None = ...) -> bytes: ...
+def tostringlist(element: Element, encoding: str | None = ..., method: str | None = ...) -> List[bytes]: ...
 def dump(elem: Element) -> None: ...
-def parse(source: _file_or_filename, parser: Optional[XMLParser] = ...) -> ElementTree: ...
+def parse(source: _file_or_filename, parser: XMLParser | None = ...) -> ElementTree: ...
 def iterparse(
-    source: _file_or_filename, events: Optional[Sequence[str]] = ..., parser: Optional[XMLParser] = ...
+    source: _file_or_filename, events: Sequence[str] | None = ..., parser: XMLParser | None = ...
 ) -> Iterator[Tuple[str, Any]]: ...
-def XML(text: _parser_input_type, parser: Optional[XMLParser] = ...) -> Element: ...
-def XMLID(text: _parser_input_type, parser: Optional[XMLParser] = ...) -> Tuple[Element, Dict[_str_result_type, Element]]: ...
+def XML(text: _parser_input_type, parser: XMLParser | None = ...) -> Element: ...
+def XMLID(text: _parser_input_type, parser: XMLParser | None = ...) -> Tuple[Element, Dict[_str_result_type, Element]]: ...
 
 # This is aliased to XML in the source.
 fromstring = XML
 
-def fromstringlist(sequence: Sequence[_parser_input_type], parser: Optional[XMLParser] = ...) -> Element: ...
+def fromstringlist(sequence: Sequence[_parser_input_type], parser: XMLParser | None = ...) -> Element: ...
 
 # This type is both not precise enough and too precise. The TreeBuilder
 # requires the elementfactory to accept tag and attrs in its args and produce
@@ -190,7 +183,7 @@ def fromstringlist(sequence: Sequence[_parser_input_type], parser: Optional[XMLP
 _ElementFactory = Callable[[Any, Dict[Any, Any]], Element]
 
 class TreeBuilder:
-    def __init__(self, element_factory: Optional[_ElementFactory] = ...) -> None: ...
+    def __init__(self, element_factory: _ElementFactory | None = ...) -> None: ...
     def close(self) -> Element: ...
     def data(self, __data: _parser_input_type) -> None: ...
     def start(self, __tag: _parser_input_type, __attrs: Dict[_parser_input_type, _parser_input_type]) -> Element: ...
@@ -202,7 +195,7 @@ class XMLParser:
     # TODO-what is entity used for???
     entity: Any
     version: str
-    def __init__(self, html: int = ..., target: Any = ..., encoding: Optional[str] = ...) -> None: ...
+    def __init__(self, html: int = ..., target: Any = ..., encoding: str | None = ...) -> None: ...
     def doctype(self, __name: str, __pubid: str, __system: str) -> None: ...
     def close(self) -> Any: ...
     def feed(self, __data: _parser_input_type) -> None: ...
diff --git a/stdlib/@python2/xml/sax/__init__.pyi b/stdlib/@python2/xml/sax/__init__.pyi
index f4ad8ba34c89..0c6da9a87d13 100644
--- a/stdlib/@python2/xml/sax/__init__.pyi
+++ b/stdlib/@python2/xml/sax/__init__.pyi
@@ -1,9 +1,9 @@
-from typing import IO, Any, List, NoReturn, Optional, Text, Union
+from typing import IO, Any, List, NoReturn, Text
 from xml.sax.handler import ContentHandler, ErrorHandler
 from xml.sax.xmlreader import Locator, XMLReader
 
 class SAXException(Exception):
-    def __init__(self, msg: str, exception: Optional[Exception] = ...) -> None: ...
+    def __init__(self, msg: str, exception: Exception | None = ...) -> None: ...
     def getMessage(self) -> str: ...
     def getException(self) -> Exception: ...
     def __getitem__(self, ix: Any) -> NoReturn: ...
@@ -22,6 +22,6 @@ class SAXReaderNotAvailable(SAXNotSupportedException): ...
 default_parser_list: List[str]
 
 def make_parser(parser_list: List[str] = ...) -> XMLReader: ...
-def parse(source: Union[str, IO[str], IO[bytes]], handler: ContentHandler, errorHandler: ErrorHandler = ...) -> None: ...
-def parseString(string: Union[bytes, Text], handler: ContentHandler, errorHandler: Optional[ErrorHandler] = ...) -> None: ...
+def parse(source: str | IO[str] | IO[bytes], handler: ContentHandler, errorHandler: ErrorHandler = ...) -> None: ...
+def parseString(string: bytes | Text, handler: ContentHandler, errorHandler: ErrorHandler | None = ...) -> None: ...
 def _create_parser(parser_name: str) -> XMLReader: ...
diff --git a/stdlib/@python2/xml/sax/saxutils.pyi b/stdlib/@python2/xml/sax/saxutils.pyi
index 3f2671eaacfe..1fc896490f54 100644
--- a/stdlib/@python2/xml/sax/saxutils.pyi
+++ b/stdlib/@python2/xml/sax/saxutils.pyi
@@ -1,7 +1,7 @@
 from _typeshed import SupportsWrite
 from codecs import StreamReaderWriter, StreamWriter
 from io import RawIOBase, TextIOBase
-from typing import Mapping, Optional, Text, Union
+from typing import Mapping, Text
 from xml.sax import handler, xmlreader
 
 def escape(data: Text, entities: Mapping[Text, Text] = ...) -> Text: ...
@@ -11,7 +11,7 @@ def quoteattr(data: Text, entities: Mapping[Text, Text] = ...) -> Text: ...
 class XMLGenerator(handler.ContentHandler):
     def __init__(
         self,
-        out: Optional[Union[TextIOBase, RawIOBase, StreamWriter, StreamReaderWriter, SupportsWrite[str]]] = ...,
+        out: TextIOBase | RawIOBase | StreamWriter | StreamReaderWriter | SupportsWrite[str] | None = ...,
         encoding: Text = ...,
     ) -> None: ...
     def startDocument(self): ...
@@ -27,7 +27,7 @@ class XMLGenerator(handler.ContentHandler):
     def processingInstruction(self, target, data): ...
 
 class XMLFilterBase(xmlreader.XMLReader):
-    def __init__(self, parent: Optional[xmlreader.XMLReader] = ...) -> None: ...
+    def __init__(self, parent: xmlreader.XMLReader | None = ...) -> None: ...
     def error(self, exception): ...
     def fatalError(self, exception): ...
     def warning(self, exception): ...
diff --git a/stdlib/@python2/xml/sax/xmlreader.pyi b/stdlib/@python2/xml/sax/xmlreader.pyi
index 9dd6b75fd52f..8afc566b16a1 100644
--- a/stdlib/@python2/xml/sax/xmlreader.pyi
+++ b/stdlib/@python2/xml/sax/xmlreader.pyi
@@ -1,4 +1,4 @@
-from typing import Mapping, Optional, Tuple
+from typing import Mapping, Tuple
 
 class XMLReader:
     def __init__(self) -> None: ...
@@ -32,7 +32,7 @@ class Locator:
     def getSystemId(self): ...
 
 class InputSource:
-    def __init__(self, system_id: Optional[str] = ...) -> None: ...
+    def __init__(self, system_id: str | None = ...) -> None: ...
     def setPublicId(self, public_id): ...
     def getPublicId(self): ...
     def setSystemId(self, system_id): ...
diff --git a/stdlib/@python2/xmlrpclib.pyi b/stdlib/@python2/xmlrpclib.pyi
index 868de39ee7f7..5a7d0fc34f0e 100644
--- a/stdlib/@python2/xmlrpclib.pyi
+++ b/stdlib/@python2/xmlrpclib.pyi
@@ -5,7 +5,7 @@ from ssl import SSLContext
 from StringIO import StringIO
 from time import struct_time
 from types import InstanceType
-from typing import IO, Any, AnyStr, Callable, Iterable, List, Mapping, MutableMapping, Optional, Tuple, Type, Union
+from typing import IO, Any, AnyStr, Callable, Iterable, List, Mapping, MutableMapping, Tuple, Type, Union
 
 _Unmarshaller = Any
 _timeTuple = Tuple[int, int, int, int, int, int, int, int, int]
@@ -52,7 +52,7 @@ Boolean: Type[bool]
 
 class DateTime:
     value: str
-    def __init__(self, value: Union[str, unicode, datetime, float, int, _timeTuple, struct_time] = ...) -> None: ...
+    def __init__(self, value: str | unicode | datetime | float | int | _timeTuple | struct_time = ...) -> None: ...
     def make_comparable(self, other: _dateTimeComp) -> Tuple[unicode, unicode]: ...
     def __lt__(self, other: _dateTimeComp) -> bool: ...
     def __le__(self, other: _dateTimeComp) -> bool: ...
@@ -67,7 +67,7 @@ class DateTime:
 
 class Binary:
     data: str
-    def __init__(self, data: Optional[str] = ...) -> None: ...
+    def __init__(self, data: str | None = ...) -> None: ...
     def __cmp__(self, other: Any) -> int: ...
     def decode(self, data: str) -> None: ...
     def encode(self, out: IO[str]) -> None: ...
@@ -97,32 +97,28 @@ class SlowParser:
 
 class Marshaller:
     memo: MutableMapping[int, Any]
-    data: Optional[str]
-    encoding: Optional[str]
+    data: str | None
+    encoding: str | None
     allow_none: bool
-    def __init__(self, encoding: Optional[str] = ..., allow_none: bool = ...) -> None: ...
+    def __init__(self, encoding: str | None = ..., allow_none: bool = ...) -> None: ...
     dispatch: Mapping[type, Callable[[Marshaller, str, Callable[[str], None]], None]]
     def dumps(
         self,
-        values: Union[
-            Iterable[
-                Union[
-                    None,
-                    int,
-                    bool,
-                    long,
-                    float,
-                    str,
-                    unicode,
-                    List[Any],
-                    Tuple[Any, ...],
-                    Mapping[Any, Any],
-                    datetime,
-                    InstanceType,
-                ]
-            ],
-            Fault,
-        ],
+        values: Iterable[
+            None
+            | int
+            | bool
+            | long
+            | float
+            | str
+            | unicode
+            | List[Any]
+            | Tuple[Any, ...]
+            | Mapping[Any, Any]
+            | datetime
+            | InstanceType
+        ]
+        | Fault,
     ) -> str: ...
     def dump_nil(self, value: None, write: Callable[[str], None]) -> None: ...
     def dump_int(self, value: int, write: Callable[[str], None]) -> None: ...
@@ -155,7 +151,7 @@ class Unmarshaller:
     def append(self, object: Any) -> None: ...
     def __init__(self, use_datetime: bool = ...) -> None: ...
     def close(self) -> Tuple[Any, ...]: ...
-    def getmethodname(self) -> Optional[str]: ...
+    def getmethodname(self) -> str | None: ...
     def xml(self, encoding: str, standalone: bool) -> None: ...
     def start(self, tag: str, attrs: Any) -> None: ...
     def data(self, text: str) -> None: ...
@@ -187,15 +183,15 @@ class MultiCall:
     def __getattr__(self, name: str) -> _MultiCallMethod: ...
     def __call__(self) -> MultiCallIterator: ...
 
-def getparser(use_datetime: bool = ...) -> Tuple[Union[ExpatParser, SlowParser], Unmarshaller]: ...
+def getparser(use_datetime: bool = ...) -> Tuple[ExpatParser | SlowParser, Unmarshaller]: ...
 def dumps(
-    params: Union[Tuple[Any, ...], Fault],
-    methodname: Optional[str] = ...,
-    methodresponse: Optional[bool] = ...,
-    encoding: Optional[str] = ...,
+    params: Tuple[Any, ...] | Fault,
+    methodname: str | None = ...,
+    methodresponse: bool | None = ...,
+    encoding: str | None = ...,
     allow_none: bool = ...,
 ) -> str: ...
-def loads(data: str, use_datetime: bool = ...) -> Tuple[Tuple[Any, ...], Optional[str]]: ...
+def loads(data: str, use_datetime: bool = ...) -> Tuple[Tuple[Any, ...], str | None]: ...
 def gzip_encode(data: str) -> str: ...
 def gzip_decode(data: str, max_decode: int = ...) -> str: ...
 
@@ -212,13 +208,13 @@ class _Method:
 class Transport:
     user_agent: str
     accept_gzip_encoding: bool
-    encode_threshold: Optional[int]
+    encode_threshold: int | None
     def __init__(self, use_datetime: bool = ...) -> None: ...
     def request(self, host: _hostDesc, handler: str, request_body: str, verbose: bool = ...) -> Tuple[Any, ...]: ...
     verbose: bool
     def single_request(self, host: _hostDesc, handler: str, request_body: str, verbose: bool = ...) -> Tuple[Any, ...]: ...
-    def getparser(self) -> Tuple[Union[ExpatParser, SlowParser], Unmarshaller]: ...
-    def get_host_info(self, host: _hostDesc) -> Tuple[str, Optional[List[Tuple[str, str]]], Optional[Mapping[Any, Any]]]: ...
+    def getparser(self) -> Tuple[ExpatParser | SlowParser, Unmarshaller]: ...
+    def get_host_info(self, host: _hostDesc) -> Tuple[str, List[Tuple[str, str]] | None, Mapping[Any, Any] | None]: ...
     def make_connection(self, host: _hostDesc) -> HTTPConnection: ...
     def close(self) -> None: ...
     def send_request(self, connection: HTTPConnection, handler: str, request_body: str) -> None: ...
@@ -228,21 +224,21 @@ class Transport:
     def parse_response(self, response: HTTPResponse) -> Tuple[Any, ...]: ...
 
 class SafeTransport(Transport):
-    def __init__(self, use_datetime: bool = ..., context: Optional[SSLContext] = ...) -> None: ...
+    def __init__(self, use_datetime: bool = ..., context: SSLContext | None = ...) -> None: ...
     def make_connection(self, host: _hostDesc) -> HTTPSConnection: ...
 
 class ServerProxy:
     def __init__(
         self,
         uri: str,
-        transport: Optional[Transport] = ...,
-        encoding: Optional[str] = ...,
+        transport: Transport | None = ...,
+        encoding: str | None = ...,
         verbose: bool = ...,
         allow_none: bool = ...,
         use_datetime: bool = ...,
-        context: Optional[SSLContext] = ...,
+        context: SSLContext | None = ...,
     ) -> None: ...
     def __getattr__(self, name: str) -> _Method: ...
-    def __call__(self, attr: str) -> Optional[Transport]: ...
+    def __call__(self, attr: str) -> Transport | None: ...
 
 Server = ServerProxy
diff --git a/stdlib/@python2/zipfile.pyi b/stdlib/@python2/zipfile.pyi
index 043aa5e342c7..5a0879492a88 100644
--- a/stdlib/@python2/zipfile.pyi
+++ b/stdlib/@python2/zipfile.pyi
@@ -1,7 +1,7 @@
 import io
 from _typeshed import StrPath
 from types import TracebackType
-from typing import IO, Any, Callable, Dict, Iterable, List, Optional, Pattern, Protocol, Sequence, Text, Tuple, Type, Union
+from typing import IO, Any, Callable, Dict, Iterable, List, Pattern, Protocol, Sequence, Text, Tuple, Type, Union
 
 _SZI = Union[Text, ZipInfo]
 _DT = Tuple[int, int, int, int, int, int]
@@ -18,7 +18,7 @@ class ZipExtFile(io.BufferedIOBase):
 
     PATTERN: Pattern[str] = ...
 
-    newlines: Optional[List[bytes]]
+    newlines: List[bytes] | None
     mode: str
     name: str
     def __init__(
@@ -26,48 +26,44 @@ class ZipExtFile(io.BufferedIOBase):
         fileobj: IO[bytes],
         mode: str,
         zipinfo: ZipInfo,
-        decrypter: Optional[Callable[[Sequence[int]], bytes]] = ...,
+        decrypter: Callable[[Sequence[int]], bytes] | None = ...,
         close_fileobj: bool = ...,
     ) -> None: ...
-    def read(self, n: Optional[int] = ...) -> bytes: ...
+    def read(self, n: int | None = ...) -> bytes: ...
     def readline(self, limit: int = ...) -> bytes: ...  # type: ignore
     def __repr__(self) -> str: ...
     def peek(self, n: int = ...) -> bytes: ...
-    def read1(self, n: Optional[int]) -> bytes: ...  # type: ignore
+    def read1(self, n: int | None) -> bytes: ...  # type: ignore
 
 class _Writer(Protocol):
     def write(self, __s: str) -> Any: ...
 
 class ZipFile:
-    filename: Optional[Text]
+    filename: Text | None
     debug: int
     comment: bytes
     filelist: List[ZipInfo]
-    fp: Optional[IO[bytes]]
+    fp: IO[bytes] | None
     NameToInfo: Dict[Text, ZipInfo]
     start_dir: int  # undocumented
-    def __init__(
-        self, file: Union[StrPath, IO[bytes]], mode: Text = ..., compression: int = ..., allowZip64: bool = ...
-    ) -> None: ...
+    def __init__(self, file: StrPath | IO[bytes], mode: Text = ..., compression: int = ..., allowZip64: bool = ...) -> None: ...
     def __enter__(self) -> ZipFile: ...
     def __exit__(
-        self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
+        self, exc_type: Type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
     def close(self) -> None: ...
     def getinfo(self, name: Text) -> ZipInfo: ...
     def infolist(self) -> List[ZipInfo]: ...
     def namelist(self) -> List[Text]: ...
-    def open(self, name: _SZI, mode: Text = ..., pwd: Optional[bytes] = ..., *, force_zip64: bool = ...) -> IO[bytes]: ...
-    def extract(self, member: _SZI, path: Optional[StrPath] = ..., pwd: Optional[bytes] = ...) -> str: ...
-    def extractall(
-        self, path: Optional[StrPath] = ..., members: Optional[Iterable[Text]] = ..., pwd: Optional[bytes] = ...
-    ) -> None: ...
+    def open(self, name: _SZI, mode: Text = ..., pwd: bytes | None = ..., *, force_zip64: bool = ...) -> IO[bytes]: ...
+    def extract(self, member: _SZI, path: StrPath | None = ..., pwd: bytes | None = ...) -> str: ...
+    def extractall(self, path: StrPath | None = ..., members: Iterable[Text] | None = ..., pwd: bytes | None = ...) -> None: ...
     def printdir(self) -> None: ...
     def setpassword(self, pwd: bytes) -> None: ...
-    def read(self, name: _SZI, pwd: Optional[bytes] = ...) -> bytes: ...
-    def testzip(self) -> Optional[str]: ...
-    def write(self, filename: StrPath, arcname: Optional[StrPath] = ..., compress_type: Optional[int] = ...) -> None: ...
-    def writestr(self, zinfo_or_arcname: _SZI, bytes: bytes, compress_type: Optional[int] = ...) -> None: ...
+    def read(self, name: _SZI, pwd: bytes | None = ...) -> bytes: ...
+    def testzip(self) -> str | None: ...
+    def write(self, filename: StrPath, arcname: StrPath | None = ..., compress_type: int | None = ...) -> None: ...
+    def writestr(self, zinfo_or_arcname: _SZI, bytes: bytes, compress_type: int | None = ...) -> None: ...
 
 class PyZipFile(ZipFile):
     def writepy(self, pathname: Text, basename: Text = ...) -> None: ...
@@ -90,13 +86,13 @@ class ZipInfo:
     CRC: int
     compress_size: int
     file_size: int
-    def __init__(self, filename: Optional[Text] = ..., date_time: Optional[_DT] = ...) -> None: ...
-    def FileHeader(self, zip64: Optional[bool] = ...) -> bytes: ...
+    def __init__(self, filename: Text | None = ..., date_time: _DT | None = ...) -> None: ...
+    def FileHeader(self, zip64: bool | None = ...) -> bytes: ...
 
 class _PathOpenProtocol(Protocol):
-    def __call__(self, mode: str = ..., pwd: Optional[bytes] = ..., *, force_zip64: bool = ...) -> IO[bytes]: ...
+    def __call__(self, mode: str = ..., pwd: bytes | None = ..., *, force_zip64: bool = ...) -> IO[bytes]: ...
 
-def is_zipfile(filename: Union[StrPath, IO[bytes]]) -> bool: ...
+def is_zipfile(filename: StrPath | IO[bytes]) -> bool: ...
 
 ZIP_STORED: int
 ZIP_DEFLATED: int
diff --git a/stdlib/@python2/zipimport.pyi b/stdlib/@python2/zipimport.pyi
index 14aa86bb90ad..bcefd6859059 100644
--- a/stdlib/@python2/zipimport.pyi
+++ b/stdlib/@python2/zipimport.pyi
@@ -1,16 +1,15 @@
 from types import CodeType, ModuleType
-from typing import Optional, Union
 
 class ZipImportError(ImportError): ...
 
 class zipimporter(object):
     archive: str
     prefix: str
-    def __init__(self, path: Union[str, bytes]) -> None: ...
-    def find_module(self, fullname: str, path: Optional[str] = ...) -> Optional[zipimporter]: ...
+    def __init__(self, path: str | bytes) -> None: ...
+    def find_module(self, fullname: str, path: str | None = ...) -> zipimporter | None: ...
     def get_code(self, fullname: str) -> CodeType: ...
     def get_data(self, pathname: str) -> str: ...
     def get_filename(self, fullname: str) -> str: ...
-    def get_source(self, fullname: str) -> Optional[str]: ...
+    def get_source(self, fullname: str) -> str | None: ...
     def is_package(self, fullname: str) -> bool: ...
     def load_module(self, fullname: str) -> ModuleType: ...
diff --git a/stdlib/@python2/zlib.pyi b/stdlib/@python2/zlib.pyi
index f33777ced457..2cee20fc0928 100644
--- a/stdlib/@python2/zlib.pyi
+++ b/stdlib/@python2/zlib.pyi
@@ -1,5 +1,5 @@
 from array import array
-from typing import Any, Union
+from typing import Any
 
 DEFLATED: int
 DEF_MEM_LEVEL: int
@@ -35,6 +35,6 @@ class _Decompress:
 def adler32(__data: bytes, __value: int = ...) -> int: ...
 def compress(__data: bytes, level: int = ...) -> bytes: ...
 def compressobj(level: int = ..., method: int = ..., wbits: int = ..., memlevel: int = ..., strategy: int = ...) -> _Compress: ...
-def crc32(__data: Union[array[Any], bytes], __value: int = ...) -> int: ...
+def crc32(__data: array[Any] | bytes, __value: int = ...) -> int: ...
 def decompress(__data: bytes, wbits: int = ..., bufsize: int = ...) -> bytes: ...
 def decompressobj(wbits: int = ...) -> _Decompress: ...