diff --git a/pyupgrade/_plugins/imports.py b/pyupgrade/_plugins/imports.py
index 6d24864a..df54d6e5 100644
--- a/pyupgrade/_plugins/imports.py
+++ b/pyupgrade/_plugins/imports.py
@@ -20,7 +20,7 @@
 from pyupgrade._token_helpers import indented_amount
 
 # GENERATED VIA generate-imports
-# Using reorder-python-imports==3.8.0
+# Using reorder-python-imports==3.8.1
 REMOVALS = {
     (2, 7): {'__future__': {'generators', 'nested_scopes', 'with_statement'}},
     (3,): {
@@ -130,7 +130,6 @@
         ('typing', 'AsyncIterator'): 'collections.abc',
         ('typing', 'Awaitable'): 'collections.abc',
         ('typing', 'ByteString'): 'collections.abc',
-        ('typing', 'Callable'): 'collections.abc',
         ('typing', 'ChainMap'): 'collections',
         ('typing', 'Collection'): 'collections.abc',
         ('typing', 'Container'): 'collections.abc',
@@ -159,6 +158,7 @@
         ('typing_extensions', 'Annotated'): 'typing',
     },
     (3, 10): {
+        ('typing', 'Callable'): 'collections.abc',
         ('typing_extensions', 'Concatenate'): 'typing',
         ('typing_extensions', 'ParamSpec'): 'typing',
         ('typing_extensions', 'TypeAlias'): 'typing',
diff --git a/tests/features/import_replaces_test.py b/tests/features/import_replaces_test.py
index d53acbe0..d0523084 100644
--- a/tests/features/import_replaces_test.py
+++ b/tests/features/import_replaces_test.py
@@ -45,6 +45,11 @@
             (3,),
             id='from import of module without alias',
         ),
+        pytest.param(
+            'from typing import Callable\n',
+            (3, 9),
+            id='skip rewriting of Callable in 3.9 since it is broken',
+        ),
     ),
 )
 def test_import_replaces_noop(s, min_version):
@@ -283,6 +288,12 @@ def test_mock_noop_keep_mock():
             'from unittest import mock\n',
             id='mock import mock import',
         ),
+        pytest.param(
+            'from typing import Callable\n',
+            (3, 10),
+            'from collections.abc import Callable\n',
+            id='typing.Callable is rewritable in 3.10+ only',
+        ),
     ),
 )
 def test_import_replaces(s, min_version, expected):