diff --git a/.flake8 b/.flake8
index e0862778a..4c8e737b8 100644
--- a/.flake8
+++ b/.flake8
@@ -19,6 +19,9 @@
 
 # Rules that we'd like to enable in the future:
 #       Y026 Use typing_extensions.TypeAlias for type aliases (blocked by #4913)
+#       Y027 Disallow importing typing.ContextManager, typing.OrderedDict &
+#            typing_extensions.OrderedDict (cannot be globally enabled while typeshed
+#            still contains stubs supporting Python 2).
 
 [flake8]
 per-file-ignores =
@@ -28,7 +31,10 @@ per-file-ignores =
   # Unfortunately, flake8 does not allow to "noqa" just a specific error inside the file itself.
   # https://github.com/PyCQA/flake8/issues/1079
   #     F811 redefinition of unused '...'
-  typing.pyi: E301, E302, E305, E501, E701, E741, F401, F403, F405, F811, F822, Y026
+  stubs/*.pyi: E301, E302, E305, E501, E701, E741, F401, F403, F405, F822, Y026, Y027
+  stdlib/@python2/*.pyi: E301, E302, E305, E501, E701, E741, F401, F403, F405, F822, Y026, Y027
+  stdlib/@python2/typing.pyi: E301, E302, E305, E501, E701, E741, F401, F403, F405, F811, F822, Y026, Y027
+  stdlib/typing.pyi: E301, E302, E305, E501, E701, E741, F401, F403, F405, F811, F822, Y026
 
 # We are checking with Python 3 but many of the stubs are Python 2 stubs.
 builtins = buffer,file,long,raw_input,unicode,xrange
diff --git a/stdlib/contextlib.pyi b/stdlib/contextlib.pyi
index 047285d89..9164227fa 100644
--- a/stdlib/contextlib.pyi
+++ b/stdlib/contextlib.pyi
@@ -1,7 +1,7 @@
 import sys
 from _typeshed import Self, StrOrBytesPath
 from types import TracebackType
-from typing import (
+from typing import (  # noqa Y027
     IO,
     Any,
     AsyncGenerator,