Jeremy <ucod...@gmail.com> added the comment:

A LBYL won't always raise errors early as you point out. It will give earlier 
warnings for a lot of cases, but makes contextlib.chdir usable in less places 
than os.chdir.
Some return paths will always be errors, and some will be technically 
recoverable but too difficult to detect and or fragile. That's why I think any 
solution should incorporate the `ignore_errors` flag. Its pretty ugly to wrap a 
context manager in a try: except: just because you were trying to clean up 
after whatever you were doing but the cwd changed in unexpected ways, maybe out 
of your control.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue45545>
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