Oldest failure seems to be https://dev.azure.com/ms/vscode-python/_build/results?buildId=88048&view=logs&j=c988df44-9d9a-569e-48be-286abc0c9c8f&t=e05b582e-afad-5edb-605e-ce81b7e22a0b for #12232 (the failure isn't related to the PR).

Seems like py==1.8.2 causes the failures, one of the last passing CI runs had py==1.8.1, and rolling back to py==1.8.1 makes the tests pass locally.

1.8.2 (2020-06-15)

On Windows, py.path.locals which differ only in case now have the same
Python hash value. Previously, such paths were considered equal but had
different hashes, which is not allowed and breaks the assumptions made by
dicts, sets and other users of hashes.

Maybe a related issue: https://github.com/pytest-dev/py/issues/245

The quickest fix would be to force py to be 1.8.1, because fixing the tests for windows (by changing the order of nodes in the array of expected results) is a Windows-specific fix that breaks Unix tests.

We could also try removing the offending test nodes and files 🙃

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