Should Path.resolve() also avoid raising OSError? Path('*').resolve() Traceback (most recent call last): ...truncated File "<ipython-input-5-4fa2fec5c8b3>", line 1, in <module> Path('*').resolve() File "C:\Users\jimbo1qaz\AppData\Local\Programs\Python\Python37\lib\pathlib.py", line 1134, in resolve s = self._flavour.resolve(self, strict=strict) File "C:\Users\jimbo1qaz\AppData\Local\Programs\Python\Python37\lib\pathlib.py", line 192, in resolve s = self._ext_to_normal(_getfinalpathname(s)) OSError: [WinError 123] The filename, directory name, or volume label syntax is incorrect: '*' os.path.realpath('"*') Out[8]: 'C:\\Users\\jimbo1qaz\\Dropbox\\encrypted\\code\\corrscope\\"*' os.path.abspath('*"') Out[13]: 'C:\\Users\\jimbo1qaz\\Dropbox\\encrypted\\code\\corrscope\\*"' (sidenote: what os.path operation does Path.resolve() match? Path('nonexistent').resolve() returns a relative path on Python 3.7.1, whereas Path().resolve() returns an absolute path.)