diff --git a/stdlib/aifc.pyi b/stdlib/aifc.pyi
index b43af47ff5e8..25df252fe30e 100644
--- a/stdlib/aifc.pyi
+++ b/stdlib/aifc.pyi
@@ -1,4 +1,5 @@
 import sys
+from _typeshed import Self
 from types import TracebackType
 from typing import IO, Any, List, NamedTuple, Optional, Tuple, Type, Union, overload
 from typing_extensions import Literal
@@ -18,7 +19,7 @@ _Marker = Tuple[int, int, bytes]
 
 class Aifc_read:
     def __init__(self, f: _File) -> None: ...
-    def __enter__(self) -> Aifc_read: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_val: Optional[BaseException], exc_tb: Optional[TracebackType]
     ) -> None: ...
@@ -42,7 +43,7 @@ class Aifc_read:
 class Aifc_write:
     def __init__(self, f: _File) -> None: ...
     def __del__(self) -> None: ...
-    def __enter__(self) -> Aifc_write: ...
+    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/asyncio/windows_utils.pyi b/stdlib/asyncio/windows_utils.pyi
index e6009d58ebc7..1d16127a5ebe 100644
--- a/stdlib/asyncio/windows_utils.pyi
+++ b/stdlib/asyncio/windows_utils.pyi
@@ -1,4 +1,5 @@
 import sys
+from _typeshed import Self
 from types import TracebackType
 from typing import Callable, Optional, Protocol, Tuple, Type
 
@@ -18,7 +19,7 @@ class PipeHandle:
         def __del__(self, _warn: _WarnFunction = ...) -> None: ...
     else:
         def __del__(self) -> None: ...
-    def __enter__(self) -> PipeHandle: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, t: Optional[type], v: Optional[BaseException], tb: Optional[TracebackType]) -> None: ...
     @property
     def handle(self) -> int: ...
diff --git a/stdlib/imaplib.pyi b/stdlib/imaplib.pyi
index 9fc3a740c463..8ad242cca0f7 100644
--- a/stdlib/imaplib.pyi
+++ b/stdlib/imaplib.pyi
@@ -1,6 +1,7 @@
 import subprocess
 import sys
 import time
+from _typeshed import Self
 from socket import socket as _socket
 from ssl import SSLContext, SSLSocket
 from types import TracebackType
@@ -59,7 +60,7 @@ class IMAP4:
     def delete(self, mailbox: str) -> _CommandResults: ...
     def deleteacl(self, mailbox: str, who: str) -> _CommandResults: ...
     def enable(self, capability: str) -> _CommandResults: ...
-    def __enter__(self) -> IMAP4: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, t: Optional[Type[BaseException]], v: Optional[BaseException], tb: Optional[TracebackType]) -> None: ...
     def expunge(self) -> _CommandResults: ...
     def fetch(self, message_set: str, message_parts: str) -> Tuple[str, _AnyResponseData]: ...
diff --git a/stdlib/multiprocessing/connection.pyi b/stdlib/multiprocessing/connection.pyi
index 15f58a3745f3..c87dd310e37f 100644
--- a/stdlib/multiprocessing/connection.pyi
+++ b/stdlib/multiprocessing/connection.pyi
@@ -1,6 +1,7 @@
 import socket
 import sys
 import types
+from _typeshed import Self
 from typing import Any, Iterable, List, Optional, Tuple, Type, Union
 
 if sys.version_info >= (3, 8):
@@ -48,7 +49,7 @@ class Listener:
     def address(self) -> _Address: ...
     @property
     def last_accepted(self) -> Optional[_Address]: ...
-    def __enter__(self) -> Listener: ...
+    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/shelve.pyi b/stdlib/shelve.pyi
index ed062f62b49b..2e36338dba70 100644
--- a/stdlib/shelve.pyi
+++ b/stdlib/shelve.pyi
@@ -1,4 +1,5 @@
 import collections.abc
+from _typeshed import Self
 from typing import Any, Dict, Iterator, Optional, Tuple
 
 class Shelf(collections.abc.MutableMapping[Any, Any]):
@@ -12,7 +13,7 @@ class Shelf(collections.abc.MutableMapping[Any, Any]):
     def __getitem__(self, key: str) -> Any: ...
     def __setitem__(self, key: str, value: Any) -> None: ...
     def __delitem__(self, key: str) -> 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/smtplib.pyi b/stdlib/smtplib.pyi
index 48a35f8e3b67..5d0ab420ee28 100644
--- a/stdlib/smtplib.pyi
+++ b/stdlib/smtplib.pyi
@@ -1,3 +1,4 @@
+from _typeshed import Self
 from email.message import Message as _Message
 from socket import socket
 from ssl import SSLContext
@@ -75,7 +76,7 @@ class SMTP:
         timeout: float = ...,
         source_address: Optional[_SourceAddress] = ...,
     ) -> None: ...
-    def __enter__(self) -> SMTP: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(
         self, exc_type: Optional[Type[BaseException]], exc_value: Optional[BaseException], tb: Optional[TracebackType]
     ) -> None: ...
diff --git a/stdlib/wave.pyi b/stdlib/wave.pyi
index 61f9136ea334..cafdcd408398 100644
--- a/stdlib/wave.pyi
+++ b/stdlib/wave.pyi
@@ -1,4 +1,5 @@
 import sys
+from _typeshed import Self
 from typing import IO, Any, BinaryIO, NamedTuple, NoReturn, Optional, Union
 
 _File = Union[str, IO[bytes]]
@@ -17,7 +18,7 @@ class _wave_params(NamedTuple):
 
 class Wave_read:
     def __init__(self, f: _File) -> None: ...
-    def __enter__(self) -> Wave_read: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, *args: Any) -> None: ...
     def getfp(self) -> Optional[BinaryIO]: ...
     def rewind(self) -> None: ...
@@ -37,7 +38,7 @@ class Wave_read:
 
 class Wave_write:
     def __init__(self, f: _File) -> None: ...
-    def __enter__(self) -> Wave_write: ...
+    def __enter__(self: Self) -> Self: ...
     def __exit__(self, *args: Any) -> None: ...
     def setnchannels(self, nchannels: int) -> None: ...
     def getnchannels(self) -> int: ...