diff --git a/pytools/tag.py b/pytools/tag.py
index 2868c4b162a9dbadc1e2011c2716bedb9238794b..8954aab7141c1a0eb1f3a8a6ffa4d8666dc46533 100644
--- a/pytools/tag.py
+++ b/pytools/tag.py
@@ -40,10 +40,16 @@ from typing import (
 from warnings import warn
 
 
-try:
-    from typing import Self, dataclass_transform
-except ImportError:
+if TYPE_CHECKING:
+    # NOTE: mypy seems to be confused by the `try.. except` below when called with
+    #   python -m mypy --python-version 3.8 ...
+    # see https://github.com/python/mypy/issues/14220
     from typing_extensions import Self, dataclass_transform
+else:
+    try:
+        from typing import Self, dataclass_transform
+    except ImportError:
+        from typing_extensions import Self, dataclass_transform
 
 from pytools import memoize, memoize_method