Jason R. Coombs added the comment:

I paused the Dropbox sync and ran the `rm -R .tox; tox` routine many times 
without incident, which strongly implicates Dropbox. I'm going to now re-enable 
Dropbox sync and see if I can trigger the behavior.

Now even with Dropbox updated back to the latest version (16.3.27) and 
performing the same operations I was two days ago, I've been unable to elicit 
the behavior. I've confirmed I still have access to delete those files that 
were being deleted, but yet I can't trigger the failure. Perhaps whatever 
environmental thing that happened on Monday was a fluke and I'll go back not to 
being bothered ever by this condition.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue28949>
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