I'm writing a program taking paths from user input through CLI. `path` is a pathlib.Path(). Since Windows doesn't expand asterisks, I check if the path doesn't exist. If so I expand using Path().glob(path). Unfortunately on Windows, if `path` (type: Path) contains asterisks, checking `path.exists()` or `path.is_dir()` raises WinError 123. Python 3.7.0 (default, Jun 28 2018, 08:04:48) [MSC v.1912 64 bit (AMD64)] :: Anaconda, Inc. on win32 Type "help", "copyright", "credits" or "license" for more information. >>> from pathlib import Path >>> Path('*').exists() Traceback (most recent call last): File "<stdin>", line 1, in <module> File "C:\Users\jimbo1qaz\Miniconda3\envs\python37\lib\pathlib.py", line 1318, in exists self.stat() File "C:\Users\jimbo1qaz\Miniconda3\envs\python37\lib\pathlib.py", line 1140, in stat return self._accessor.stat(self) OSError: [WinError 123] The filename, directory name, or volume label syntax is incorrect: '*' >>> Path('*').is_dir() Traceback (most recent call last): File "<stdin>", line 1, in <module> File "C:\Users\jimbo1qaz\Miniconda3\envs\python37\lib\pathlib.py", line 1330, in is_dir return S_ISDIR(self.stat().st_mode) File "C:\Users\jimbo1qaz\Miniconda3\envs\python37\lib\pathlib.py", line 1140, in stat return self._accessor.stat(self) OSError: [WinError 123] The filename, directory name, or volume label syntax is incorrect: '*' I also reproduced on Miniconda 3.6.6, 3.7.0, and official Python 3.7.1. According to https://bugs.python.org/issue29827 , os.path.exists() (not Path.exists() ) returns False on any OSError. ----------------- On Linux, checking paths with null bytes (a less common occurrence) raises a different error: >>> import pathlib >>> pathlib.Path("\x00").exists() Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/usr/lib/python3.6/pathlib.py", line 1336, in exists self.stat() File "/usr/lib/python3.6/pathlib.py", line 1158, in stat return self._accessor.stat(self) File "/usr/lib/python3.6/pathlib.py", line 387, in wrapped return strfunc(str(pathobj), *args) ValueError: embedded null byte