Jeffrey Kintscher <websur...@surf2c.net> added the comment:

I implemented an onerror callback for tempfile.TemporaryDirectory() and 
confirmed that it cannot be used to unmount a mount point.  Attempting to 
unmount the mount point from within the callback results in a resource busy 
error.  It may be related to shutil.rmtree() holding an open file descriptor to 
the parent directory of the mount point.

I uploaded the program I used for testing on macOS (test-mounted-image.py). The 
subprocess.run() calls can be modified to run it on other platforms.

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Added file: https://bugs.python.org/file48429/test-mounted-image.py

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<https://bugs.python.org/issue36422>
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