diff --git a/stdlib/@python2/__builtin__.pyi b/stdlib/@python2/__builtin__.pyi
index d5e1c2e5e53b..0039adaaacb3 100644
--- a/stdlib/@python2/__builtin__.pyi
+++ b/stdlib/@python2/__builtin__.pyi
@@ -751,7 +751,7 @@ class frozenset(AbstractSet[_T_co], Generic[_T_co]):
 
 class enumerate(Iterator[tuple[int, _T]], Generic[_T]):
     def __init__(self, iterable: Iterable[_T], start: int = ...) -> None: ...
-    def __iter__(self) -> Iterator[tuple[int, _T]]: ...
+    def __iter__(self: Self) -> Self: ...
     def next(self) -> tuple[int, _T]: ...
 
 class xrange(Sized, Iterable[int], Reversible[int]):
diff --git a/stdlib/@python2/_winreg.pyi b/stdlib/@python2/_winreg.pyi
index 0381dc03ba01..e432d883e4d5 100644
--- a/stdlib/@python2/_winreg.pyi
+++ b/stdlib/@python2/_winreg.pyi
@@ -1,4 +1,5 @@
 import sys
+from _typeshed import Self
 from types import TracebackType
 from typing import Any, Union
 
@@ -88,7 +89,7 @@ if sys.platform == "win32":
     class HKEYType:
         def __bool__(self) -> bool: ...
         def __int__(self) -> int: ...
-        def __enter__(self) -> HKEYType: ...
+        def __enter__(self: Self) -> Self: ...
         def __exit__(
             self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
         ) -> bool | None: ...
diff --git a/stdlib/@python2/builtins.pyi b/stdlib/@python2/builtins.pyi
index d5e1c2e5e53b..0039adaaacb3 100644
--- a/stdlib/@python2/builtins.pyi
+++ b/stdlib/@python2/builtins.pyi
@@ -751,7 +751,7 @@ class frozenset(AbstractSet[_T_co], Generic[_T_co]):
 
 class enumerate(Iterator[tuple[int, _T]], Generic[_T]):
     def __init__(self, iterable: Iterable[_T], start: int = ...) -> None: ...
-    def __iter__(self) -> Iterator[tuple[int, _T]]: ...
+    def __iter__(self: Self) -> Self: ...
     def next(self) -> tuple[int, _T]: ...
 
 class xrange(Sized, Iterable[int], Reversible[int]):
diff --git a/stdlib/@python2/codecs.pyi b/stdlib/@python2/codecs.pyi
index 339578ca1ae7..2780d473b781 100644
--- a/stdlib/@python2/codecs.pyi
+++ b/stdlib/@python2/codecs.pyi
@@ -85,7 +85,7 @@ class CodecInfo(tuple[_Encoder, _Decoder, _StreamReader, _StreamWriter]):
     def incrementaldecoder(self) -> _IncrementalDecoder: ...
     name: str
     def __new__(
-        cls,
+        cls: type[Self],
         encode: _Encoder,
         decode: _Decoder,
         streamreader: _StreamReader | None = ...,
@@ -95,7 +95,7 @@ class CodecInfo(tuple[_Encoder, _Decoder, _StreamReader, _StreamWriter]):
         name: str | None = ...,
         *,
         _is_text_encoding: bool | None = ...,
-    ) -> CodecInfo: ...
+    ) -> Self: ...
 
 def getencoder(encoding: str) -> _Encoder: ...
 def getdecoder(encoding: str) -> _Decoder: ...
diff --git a/stdlib/@python2/dbm/__init__.pyi b/stdlib/@python2/dbm/__init__.pyi
index 738c60792a4e..9c867074df06 100644
--- a/stdlib/@python2/dbm/__init__.pyi
+++ b/stdlib/@python2/dbm/__init__.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from types import TracebackType
 from typing import Iterator, MutableMapping, Union
 from typing_extensions import Literal
@@ -13,7 +14,7 @@ class _Database(MutableMapping[_KeyType, bytes]):
     def __iter__(self) -> Iterator[bytes]: ...
     def __len__(self) -> int: ...
     def __del__(self) -> None: ...
-    def __enter__(self) -> _Database: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
diff --git a/stdlib/@python2/dbm/dumb.pyi b/stdlib/@python2/dbm/dumb.pyi
index 163ceb53d685..e040f23ce2b0 100644
--- a/stdlib/@python2/dbm/dumb.pyi
+++ b/stdlib/@python2/dbm/dumb.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from types import TracebackType
 from typing import Iterator, MutableMapping, Union
 
@@ -17,7 +18,7 @@ class _Database(MutableMapping[_KeyType, bytes]):
     def __iter__(self) -> Iterator[bytes]: ...
     def __len__(self) -> int: ...
     def __del__(self) -> None: ...
-    def __enter__(self) -> _Database: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
diff --git a/stdlib/@python2/dbm/gnu.pyi b/stdlib/@python2/dbm/gnu.pyi
index b8b10cb62b3e..1eecfac66a5f 100644
--- a/stdlib/@python2/dbm/gnu.pyi
+++ b/stdlib/@python2/dbm/gnu.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from types import TracebackType
 from typing import TypeVar, Union, overload
 
@@ -18,7 +19,7 @@ class _gdbm:
     def __setitem__(self, key: _KeyType, value: _ValueType) -> None: ...
     def __delitem__(self, key: _KeyType) -> None: ...
     def __len__(self) -> int: ...
-    def __enter__(self) -> _gdbm: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
diff --git a/stdlib/@python2/dbm/ndbm.pyi b/stdlib/@python2/dbm/ndbm.pyi
index dec50baaaaf4..12d9f31881c1 100644
--- a/stdlib/@python2/dbm/ndbm.pyi
+++ b/stdlib/@python2/dbm/ndbm.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from types import TracebackType
 from typing import TypeVar, Union, overload
 
@@ -17,7 +18,7 @@ class _dbm:
     def __delitem__(self, key: _KeyType) -> None: ...
     def __len__(self) -> int: ...
     def __del__(self) -> None: ...
-    def __enter__(self) -> _dbm: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
diff --git a/stdlib/@python2/itertools.pyi b/stdlib/@python2/itertools.pyi
index c16ca8debb03..6509213e1625 100644
--- a/stdlib/@python2/itertools.pyi
+++ b/stdlib/@python2/itertools.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from typing import Any, Callable, Generic, Iterable, Iterator, Sequence, TypeVar, overload
 
 _T = TypeVar("_T")
@@ -8,14 +9,14 @@ def count(start: int = ..., step: int = ...) -> Iterator[int]: ...  # more gener
 class cycle(Iterator[_T], Generic[_T]):
     def __init__(self, iterable: Iterable[_T]) -> None: ...
     def next(self) -> _T: ...
-    def __iter__(self) -> Iterator[_T]: ...
+    def __iter__(self: Self) -> Self: ...
 
 def repeat(object: _T, times: int = ...) -> Iterator[_T]: ...
 
 class chain(Iterator[_T], Generic[_T]):
     def __init__(self, *iterables: Iterable[_T]) -> None: ...
     def next(self) -> _T: ...
-    def __iter__(self) -> Iterator[_T]: ...
+    def __iter__(self: Self) -> Self: ...
     @staticmethod
     def from_iterable(iterable: Iterable[Iterable[_S]]) -> Iterator[_S]: ...
 
diff --git a/stdlib/@python2/multiprocessing/pool.pyi b/stdlib/@python2/multiprocessing/pool.pyi
index 3a1245fe1b7f..440b5e83c500 100644
--- a/stdlib/@python2/multiprocessing/pool.pyi
+++ b/stdlib/@python2/multiprocessing/pool.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from typing import Any, Callable, Iterable, Iterator
 
 class AsyncResult:
@@ -7,7 +8,7 @@ class AsyncResult:
     def successful(self) -> bool: ...
 
 class IMapIterator(Iterator[Any]):
-    def __iter__(self) -> Iterator[Any]: ...
+    def __iter__(self: Self) -> Self: ...
     def next(self, timeout: float | None = ...) -> Any: ...
 
 class IMapUnorderedIterator(IMapIterator): ...
diff --git a/stdlib/@python2/shelve.pyi b/stdlib/@python2/shelve.pyi
index 0e795c4148a7..011159792e60 100644
--- a/stdlib/@python2/shelve.pyi
+++ b/stdlib/@python2/shelve.pyi
@@ -1,4 +1,5 @@
 import collections
+from _typeshed import Self
 from typing import Any, Iterator
 
 class Shelf(collections.MutableMapping[Any, Any]):
@@ -14,7 +15,7 @@ class Shelf(collections.MutableMapping[Any, Any]):
     def __getitem__(self, key: Any) -> Any: ...
     def __setitem__(self, key: Any, value: Any) -> None: ...
     def __delitem__(self, key: Any) -> None: ...
-    def __enter__(self) -> Shelf: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, type: Any, value: Any, traceback: Any) -> None: ...
     def close(self) -> None: ...
     def __del__(self) -> None: ...
diff --git a/stdlib/@python2/sqlite3/dbapi2.pyi b/stdlib/@python2/sqlite3/dbapi2.pyi
index 37b3b6df71b0..90740bcf90a1 100644
--- a/stdlib/@python2/sqlite3/dbapi2.pyi
+++ b/stdlib/@python2/sqlite3/dbapi2.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from datetime import date, datetime, time
 from typing import Any, Callable, Generator, Iterable, Iterator, Protocol, Text, TypeVar
 
@@ -126,7 +127,7 @@ class Connection(object):
     def enable_load_extension(self, enabled: bool) -> None: ...
     def load_extension(self, path: str) -> None: ...
     def __call__(self, *args: Any, **kwargs: Any) -> Any: ...
-    def __enter__(self) -> Connection: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, t: type | None, exc: BaseException | None, tb: Any | None) -> None: ...
 
 class Cursor(Iterator[Any]):
diff --git a/stdlib/@python2/ssl.pyi b/stdlib/@python2/ssl.pyi
index 67ba3bb18bdd..4eccf5875d55 100644
--- a/stdlib/@python2/ssl.pyi
+++ b/stdlib/@python2/ssl.pyi
@@ -1,6 +1,6 @@
 import socket
 import sys
-from _typeshed import StrPath
+from _typeshed import Self, StrPath
 from typing import Any, Callable, ClassVar, Iterable, NamedTuple, Optional, Text, Union, overload
 from typing_extensions import Literal
 
@@ -213,7 +213,7 @@ class SSLSocket(socket.socket):
 class SSLContext:
     check_hostname: bool
     options: int
-    def __new__(cls, protocol: int, *args: Any, **kwargs: Any) -> SSLContext: ...
+    def __new__(cls: type[Self], protocol: int, *args: Any, **kwargs: Any) -> Self: ...
     @property
     def protocol(self) -> int: ...
     verify_flags: int
diff --git a/stdlib/@python2/tarfile.pyi b/stdlib/@python2/tarfile.pyi
index 4f1efe5e4070..571bb19632a8 100644
--- a/stdlib/@python2/tarfile.pyi
+++ b/stdlib/@python2/tarfile.pyi
@@ -1,4 +1,5 @@
 import io
+from _typeshed import Self
 from types import TracebackType
 from typing import IO, Callable, Iterable, Iterator, Mapping, Text
 
@@ -103,7 +104,7 @@ class TarFile(Iterable[TarInfo]):
         errorlevel: int | None = ...,
         copybufsize: int | None = ...,  # undocumented
     ) -> None: ...
-    def __enter__(self) -> TarFile: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...
diff --git a/stdlib/@python2/tempfile.pyi b/stdlib/@python2/tempfile.pyi
index 25397d130165..3d94bdefeb74 100644
--- a/stdlib/@python2/tempfile.pyi
+++ b/stdlib/@python2/tempfile.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from random import Random
 from thread import LockType
 from typing import IO, Any, AnyStr, Iterable, Iterator, Text, overload
@@ -23,7 +24,7 @@ class _TemporaryFileWrapper(IO[str]):
     name: Any
     def __init__(self, file: IO[str], name: Any, delete: bool = ...) -> None: ...
     def __del__(self) -> None: ...
-    def __enter__(self) -> _TemporaryFileWrapper: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, exc, value, tb) -> bool | None: ...
     def __getattr__(self, name: unicode) -> Any: ...
     def close(self) -> None: ...
diff --git a/stdlib/@python2/thread.pyi b/stdlib/@python2/thread.pyi
index b3ba062a498e..9823dddcbfd7 100644
--- a/stdlib/@python2/thread.pyi
+++ b/stdlib/@python2/thread.pyi
@@ -1,9 +1,11 @@
 from typing import Any, Callable
+from typing_extensions import final
 
 def _count() -> int: ...
 
 class error(Exception): ...
 
+@final
 class LockType:
     def acquire(self, waitflag: int = ...) -> bool: ...
     def acquire_lock(self, waitflag: int = ...) -> bool: ...
diff --git a/stdlib/@python2/time.pyi b/stdlib/@python2/time.pyi
index cbe5d63017b0..93cdafa7cafa 100644
--- a/stdlib/@python2/time.pyi
+++ b/stdlib/@python2/time.pyi
@@ -1,5 +1,6 @@
 import sys
 from typing import Any, NamedTuple
+from typing_extensions import final
 
 _TimeTuple = tuple[int, int, int, int, int, int, int, int, int]
 
@@ -26,6 +27,7 @@ class _struct_time(NamedTuple):
     @property
     def n_unnamed_fields(self) -> int: ...
 
+@final
 class struct_time(_struct_time):
     def __init__(self, o: _TimeTuple, _arg: Any = ...) -> None: ...
     def __new__(cls, o: _TimeTuple, _arg: Any = ...) -> struct_time: ...
diff --git a/stdlib/@python2/unittest.pyi b/stdlib/@python2/unittest.pyi
index 5a3084c391f6..9db413d996bb 100644
--- a/stdlib/@python2/unittest.pyi
+++ b/stdlib/@python2/unittest.pyi
@@ -1,5 +1,6 @@
 import datetime
 import types
+from _typeshed import Self
 from abc import ABCMeta, abstractmethod
 from typing import Any, Callable, Iterable, Iterator, Mapping, NoReturn, Pattern, Sequence, Text, TextIO, TypeVar, Union, overload
 from typing_extensions import ParamSpec
@@ -54,7 +55,7 @@ class _AssertRaisesBaseContext:
 
 class _AssertRaisesContext(_AssertRaisesBaseContext):
     exception: Any
-    def __enter__(self) -> _AssertRaisesContext: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, exc_type, exc_value, tb) -> bool: ...
 
 class TestCase(Testable):
diff --git a/stdlib/@python2/zipfile.pyi b/stdlib/@python2/zipfile.pyi
index b5db240bd89e..0f376d2d93b8 100644
--- a/stdlib/@python2/zipfile.pyi
+++ b/stdlib/@python2/zipfile.pyi
@@ -1,5 +1,5 @@
 import io
-from _typeshed import StrPath
+from _typeshed import Self, StrPath
 from types import TracebackType
 from typing import IO, Any, Callable, Iterable, Pattern, Protocol, Sequence, Text, Union
 
@@ -46,7 +46,7 @@ class ZipFile:
     NameToInfo: dict[Text, ZipInfo]
     start_dir: int  # undocumented
     def __init__(self, file: StrPath | IO[bytes], mode: Text = ..., compression: int = ..., allowZip64: bool = ...) -> None: ...
-    def __enter__(self) -> ZipFile: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
     ) -> None: ...