My last comment was wrong, the issue I linked is unrelated.

I think the actual issue here is the code here:
https://github.com/python/cpython/blob/4b97d974ecca9cce532be55410fe851eb9fdcf21/Lib/tempfile.py#L826

If `path` is a file that causes a permission error, `rmtree` is called and causes a NotADirectory error.

This can be confusing when debugging and can lead to a bug if user's code tries to catch a PermissionError it expects but instead gets NotADirectory error.

A solution is probably to check if path is a file and error is PermissionError and if ignore_errors=False, re-raise it instead of calling rmtree(). If ignore_errors=True, return instead of calling rmtree().

I don't have windows so can't test the OP code with this approach.

Serhiy: adding you since you wrote `def onerror()` in tempfile module, do you think that is the cause of the issue and the right solution for it?