bpo-43153: Don't mask PermissionError with NotADirectoryError during tempdirectory cleanup

Lib/tempfile.py

@@ -822,8 +822,15 @@ def resetperms(path):
 
                     try:
                         _os.unlink(path)
+                    except IsADirectoryError:
+                        cls._rmtree(path, ignore_errors=ignore_errors)
                     # PermissionError is raised on FreeBSD for directories
-                    except (IsADirectoryError, PermissionError):
+                    except PermissionError:
+                        # On Windows, _rmtree will cause IsADirectoryError
+                        if _os.name == 'nt' and _os.path.isfile(path):
+                            if ignore_errors:
+                                return
+                            raise
                         cls._rmtree(path, ignore_errors=ignore_errors)
                 except FileNotFoundError:
                     pass

Lib/test/test_tempfile.py

@@ -1460,6 +1460,16 @@ def test_explict_cleanup_ignore_errors(self):
                 temp_path.exists(),
                 f"TemporaryDirectory {temp_path!s} exists after cleanup")
 
+    @unittest.skipUnless(os.name == "nt", "Only on Windows.")
+    def test_explicit_cleanup_correct_error(self):
+        with tempfile.TemporaryDirectory() as working_dir:
+            temp_dir = self.do_create(dir=working_dir)
+            with open(os.path.join(temp_dir.name, "example.txt"), 'wb'):
+                # Used to raise IsADirectoryError on Windows.
+                with self.assertRaises(PermissionError):
+                    temp_dir.cleanup()
+
+
     @os_helper.skip_unless_symlink
     def test_cleanup_with_symlink_to_a_directory(self):
         # cleanup() should not follow symlinks to directories (issue #12464)

Misc/NEWS.d/next/Library/2021-12-06-22-10-53.bpo-43153.J7mjSy.rst

@@ -0,0 +1,4 @@
+On Windows, ``tempfile.TemporaryDirectory`` previously masked a
+``PermissionError`` with ``NotADirectoryError`` during directory cleanup. It
+now correctly raises ``PermissionError`` if errors are not ignored. Patch by
+Andrei Kulakov and Ken Jin.