Somehow I managed to trigger this bug in two typeshed pull requests: https://github.com/python/typeshed/pull/5349 and https://github.com/python/typeshed/pull/5350 The error messages are visible in typeshed CI, but if needed, I can try to make a minimal reproducing example.