diff --git a/stdlib/@tests/stubtest_allowlists/common.txt b/stdlib/@tests/stubtest_allowlists/common.txt
index 36b7bf39b6c9..413fa4f135e4 100644
--- a/stdlib/@tests/stubtest_allowlists/common.txt
+++ b/stdlib/@tests/stubtest_allowlists/common.txt
@@ -619,6 +619,31 @@ tkinter.Place.place_slaves
 tkinter.Place.slaves
 
 # Methods that come from __getattr__() at runtime
+os._wrap_close.__del__
+os._wrap_close.buffer
+os._wrap_close.closed
+os._wrap_close.detach
+os._wrap_close.encoding
+os._wrap_close.errors
+os._wrap_close.fileno
+os._wrap_close.flush
+os._wrap_close.isatty
+os._wrap_close.line_buffering
+os._wrap_close.name
+os._wrap_close.newlines
+os._wrap_close.read
+os._wrap_close.readable
+os._wrap_close.readline
+os._wrap_close.readlines
+os._wrap_close.reconfigure
+os._wrap_close.seek
+os._wrap_close.seekable
+os._wrap_close.tell
+os._wrap_close.truncate
+os._wrap_close.writable
+os._wrap_close.write
+os._wrap_close.write_through
+os._wrap_close.writelines
 tkinter.Tk.adderrorinfo
 tkinter.Tk.call
 tkinter.Tk.createcommand
diff --git a/stdlib/os/__init__.pyi b/stdlib/os/__init__.pyi
index d7bb4883a0f2..c7a413a55b2e 100644
--- a/stdlib/os/__init__.pyi
+++ b/stdlib/os/__init__.pyi
@@ -23,8 +23,9 @@ from abc import abstractmethod
 from builtins import OSError
 from collections.abc import Callable, Iterable, Iterator, Mapping, MutableMapping, Sequence
 from contextlib import AbstractContextManager
-from io import BufferedRandom, BufferedReader, BufferedWriter, FileIO, TextIOWrapper as _TextIOWrapper
+from io import BufferedRandom, BufferedReader, BufferedWriter, FileIO, TextIOWrapper, _WrappedBuffer
 from subprocess import Popen
+from types import TracebackType
 from typing import (
     IO,
     Any,
@@ -53,6 +54,7 @@ path = _path
 _T = TypeVar("_T")
 _T1 = TypeVar("_T1")
 _T2 = TypeVar("_T2")
+_BufferT_co = TypeVar("_BufferT_co", bound=_WrappedBuffer, default=_WrappedBuffer, covariant=True)
 
 # ----- os variables -----
 
@@ -578,7 +580,7 @@ def fdopen(
     newline: str | None = ...,
     closefd: bool = ...,
     opener: _Opener | None = ...,
-) -> _TextIOWrapper: ...
+) -> TextIOWrapper: ...
 @overload
 def fdopen(
     fd: int,
@@ -917,11 +919,19 @@ if sys.platform != "win32":
     if sys.platform != "darwin" and sys.platform != "linux":
         def plock(op: int, /) -> None: ...
 
-class _wrap_close(_TextIOWrapper):
-    def __init__(self, stream: _TextIOWrapper, proc: Popen[str]) -> None: ...
+class _wrap_close(Generic[_BufferT_co]):
+    def __init__(self, stream: TextIOWrapper, proc: Popen[str]) -> None: ...
     def close(self) -> int | None: ...  # type: ignore[override]
+    def __enter__(self) -> Self: ...
+    def __exit__(
+        self, exc_type: type[BaseException] | None, exc_val: BaseException | None, exc_tb: TracebackType | None
+    ) -> None: ...
+    def __iter__(self) -> Iterator[str]: ...
 
-def popen(cmd: str, mode: str = "r", buffering: int = -1) -> _wrap_close: ...
+@overload
+def popen(cmd: str, mode: Literal["r"] = "r", buffering: int = -1) -> _wrap_close[BufferedReader]: ...
+@overload
+def popen(cmd: str, mode: Literal["w"], buffering: int = -1) -> _wrap_close[BufferedWriter]: ...
 def spawnl(mode: int, file: StrOrBytesPath, arg0: StrOrBytesPath, *args: StrOrBytesPath) -> int: ...
 def spawnle(mode: int, file: StrOrBytesPath, arg0: StrOrBytesPath, *args: Any) -> int: ...  # Imprecise sig