Bo Anderson <b...@toxicflames.co.uk> added the comment:

For what it's worth, this is having an impact on some real code: 
https://github.com/Homebrew/homebrew-core/pull/45110

Perhaps a simpler way to reproduce is:

% cd /tmp
% python3 -c 'import os; open(os.path.relpath("/tmp/test.txt"), "w")'
Traceback (most recent call last):
  File "<string>", line 1, in <module>
FileNotFoundError: [Errno 2] No such file or directory: '../../tmp/test.txt'

----------
nosy: +Bo98

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue38295>
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