diff --git a/stdlib/http/client.pyi b/stdlib/http/client.pyi
index c35228928d77..1914daf1d93c 100644
--- a/stdlib/http/client.pyi
+++ b/stdlib/http/client.pyi
@@ -3,7 +3,7 @@ import io
 import ssl
 import sys
 import types
-from _typeshed import WriteableBuffer
+from _typeshed import Self, WriteableBuffer
 from socket import socket
 from typing import (
     IO,
@@ -115,7 +115,7 @@ class HTTPResponse(io.BufferedIOBase, BinaryIO):
     def fileno(self) -> int: ...
     def isclosed(self) -> bool: ...
     def __iter__(self) -> Iterator[bytes]: ...
-    def __enter__(self) -> HTTPResponse: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[types.TracebackType]
     ) -> Optional[bool]: ...
diff --git a/stdlib/multiprocessing/connection.pyi b/stdlib/multiprocessing/connection.pyi
index c87dd310e37f..ce56bea53bd7 100644
--- a/stdlib/multiprocessing/connection.pyi
+++ b/stdlib/multiprocessing/connection.pyi
@@ -29,7 +29,7 @@ class _ConnectionBase:
     def recv_bytes_into(self, buf: Any, offset: int = ...) -> int: ...
     def recv(self) -> Any: ...
     def poll(self, timeout: Optional[float] = ...) -> bool: ...
-    def __enter__(self) -> _ConnectionBase: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_value: Optional[BaseException], exc_tb: Optional[types.TracebackType]
     ) -> None: ...
diff --git a/stdlib/multiprocessing/dummy/connection.pyi b/stdlib/multiprocessing/dummy/connection.pyi
index 01733e59c763..d3abec749cde 100644
--- a/stdlib/multiprocessing/dummy/connection.pyi
+++ b/stdlib/multiprocessing/dummy/connection.pyi
@@ -1,11 +1,10 @@
+from _typeshed import Self
 from queue import Queue
 from types import TracebackType
-from typing import Any, List, Optional, Tuple, Type, TypeVar, Union
+from typing import Any, List, Optional, Tuple, Type, Union
 
 families: List[None]
 
-_ConnectionT = TypeVar("_ConnectionT", bound=Connection)
-_ListenerT = TypeVar("_ListenerT", bound=Listener)
 _Address = Union[str, Tuple[str, int]]
 
 class Connection(object):
@@ -15,7 +14,7 @@ class Connection(object):
     recv_bytes: Any
     send: Any
     send_bytes: Any
-    def __enter__(self: _ConnectionT) -> _ConnectionT: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
     ) -> None: ...
@@ -27,7 +26,7 @@ class Listener(object):
     _backlog_queue: Optional[Queue[Any]]
     @property
     def address(self) -> Optional[Queue[Any]]: ...
-    def __enter__(self: _ListenerT) -> _ListenerT: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
     ) -> None: ...
diff --git a/stdlib/multiprocessing/pool.pyi b/stdlib/multiprocessing/pool.pyi
index d8004655cacf..0f4d33dc376f 100644
--- a/stdlib/multiprocessing/pool.pyi
+++ b/stdlib/multiprocessing/pool.pyi
@@ -1,4 +1,5 @@
 import sys
+from _typeshed import Self
 from typing import Any, Callable, ContextManager, Generic, Iterable, Iterator, List, Mapping, Optional, TypeVar
 
 if sys.version_info >= (3, 9):
@@ -77,7 +78,7 @@ class Pool(ContextManager[Pool]):
     def close(self) -> None: ...
     def terminate(self) -> None: ...
     def join(self) -> None: ...
-    def __enter__(self: _PT) -> _PT: ...
+    def __enter__(self: Self) -> Self: ...
 
 class ThreadPool(Pool, ContextManager[ThreadPool]):
     def __init__(
diff --git a/stdlib/os/__init__.pyi b/stdlib/os/__init__.pyi
index 5de46ca031d7..24c6d7000e58 100644
--- a/stdlib/os/__init__.pyi
+++ b/stdlib/os/__init__.pyi
@@ -6,6 +6,7 @@ from _typeshed import (
     OpenBinaryModeUpdating,
     OpenBinaryModeWriting,
     OpenTextMode,
+    Self,
     StrOrBytesPath,
     StrPath,
 )
@@ -860,7 +861,7 @@ if sys.version_info >= (3, 8):
             path: Optional[str]
             def __init__(self, path: Optional[str], cookie: _T, remove_dll_directory: Callable[[_T], Any]) -> None: ...
             def close(self) -> None: ...
-            def __enter__(self: _T) -> _T: ...
+            def __enter__(self: Self) -> Self: ...
             def __exit__(self, *args: Any) -> None: ...
         def add_dll_directory(path: str) -> _AddedDllDirectory: ...
     if sys.platform == "linux":
diff --git a/stdlib/sqlite3/dbapi2.pyi b/stdlib/sqlite3/dbapi2.pyi
index c53141856ca8..3fb72de659d2 100644
--- a/stdlib/sqlite3/dbapi2.pyi
+++ b/stdlib/sqlite3/dbapi2.pyi
@@ -1,5 +1,5 @@
 import sys
-from _typeshed import StrOrBytesPath
+from _typeshed import Self, StrOrBytesPath
 from datetime import date, datetime, time
 from typing import Any, Callable, Generator, Iterable, Iterator, List, Optional, Protocol, Tuple, Type, TypeVar, Union
 
@@ -158,7 +158,7 @@ class Connection(object):
             sleep: float = ...,
         ) -> None: ...
     def __call__(self, *args: Any, **kwargs: Any) -> Any: ...
-    def __enter__(self) -> Connection: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, t: Optional[type], exc: Optional[BaseException], tb: Optional[Any]) -> None: ...
 
 class Cursor(Iterator[Any]):
diff --git a/stdlib/unittest/case.pyi b/stdlib/unittest/case.pyi
index 16036264af11..79a7e79069af 100644
--- a/stdlib/unittest/case.pyi
+++ b/stdlib/unittest/case.pyi
@@ -2,6 +2,7 @@ import datetime
 import logging
 import sys
 import unittest.result
+from _typeshed import Self
 from collections.abc import Set
 from types import TracebackType
 from typing import (
@@ -14,6 +15,7 @@ from typing import (
     Iterable,
     List,
     Mapping,
+    NamedTuple,
     NoReturn,
     Optional,
     Pattern,
@@ -251,9 +253,13 @@ class FunctionTestCase(TestCase):
     ) -> None: ...
     def runTest(self) -> None: ...
 
+class _LoggingWatcher(NamedTuple):
+    records: List[logging.LogRecord]
+    output: List[str]
+
 class _AssertRaisesContext(Generic[_E]):
     exception: _E
-    def __enter__(self) -> _AssertRaisesContext[_E]: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
     ) -> bool: ...
@@ -265,7 +271,7 @@ class _AssertWarnsContext:
     filename: str
     lineno: int
     warnings: List[WarningMessage]
-    def __enter__(self) -> _AssertWarnsContext: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
     ) -> None: ...
@@ -275,7 +281,10 @@ class _AssertLogsContext:
     records: List[logging.LogRecord]
     output: List[str]
     def __init__(self, test_case: TestCase, logger_name: str, level: int) -> None: ...
-    def __enter__(self) -> _AssertLogsContext: ...
+    if sys.version_info >= (3, 10):
+        def __enter__(self) -> _LoggingWatcher | None: ...
+    else:
+        def __enter__(self) -> _LoggingWatcher: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
     ) -> Optional[bool]: ...
diff --git a/stdlib/urllib/response.pyi b/stdlib/urllib/response.pyi
index c8f9d75d2f14..300105076048 100644
--- a/stdlib/urllib/response.pyi
+++ b/stdlib/urllib/response.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from email.message import Message
 from types import TracebackType
 from typing import IO, Any, BinaryIO, Callable, Iterable, List, Optional, Tuple, Type, TypeVar
@@ -7,7 +8,7 @@ _AIUT = TypeVar("_AIUT", bound=addbase)
 class addbase(BinaryIO):
     fp: IO[bytes]
     def __init__(self, fp: IO[bytes]) -> None: ...
-    def __enter__(self: _AIUT) -> _AIUT: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, type: Optional[Type[BaseException]], value: Optional[BaseException], traceback: Optional[TracebackType]
     ) -> None: ...
diff --git a/stdlib/xml/dom/minidom.pyi b/stdlib/xml/dom/minidom.pyi
index 90396299effc..a9ae79c01902 100644
--- a/stdlib/xml/dom/minidom.pyi
+++ b/stdlib/xml/dom/minidom.pyi
@@ -1,11 +1,10 @@
 import sys
 import xml.dom
-from typing import IO, Any, Optional, TypeVar, Union
+from _typeshed import Self
+from typing import IO, Any, Optional, Union
 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[str, bytes], parser: Optional[XMLReader] = ...): ...
 def getDOMImplementation(features=...): ...
@@ -39,7 +38,7 @@ class Node(xml.dom.Node):
     def setUserData(self, key, data, handler): ...
     childNodes: Any
     def unlink(self) -> None: ...
-    def __enter__(self: _T) -> _T: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, et, ev, tb) -> None: ...
 
 class DocumentFragment(Node):
diff --git a/stdlib/xmlrpc/client.pyi b/stdlib/xmlrpc/client.pyi
index b0c615063729..8844b875950e 100644
--- a/stdlib/xmlrpc/client.pyi
+++ b/stdlib/xmlrpc/client.pyi
@@ -2,7 +2,7 @@ import gzip
 import http.client
 import sys
 import time
-from _typeshed import SupportsRead, SupportsWrite
+from _typeshed import Self, SupportsRead, SupportsWrite
 from datetime import datetime
 from io import BytesIO
 from types import TracebackType
@@ -301,7 +301,7 @@ class ServerProxy:
     def __call__(self, attr: Literal["transport"]) -> Transport: ...
     @overload
     def __call__(self, attr: str) -> Union[Callable[[], None], Transport]: ...
-    def __enter__(self) -> ServerProxy: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
     ) -> None: ...