Serhiy Storchaka <storchaka+cpyt...@gmail.com> added the comment:

If you want the conditional cleanup, then TemporaryDirectory is obviously a 
wrong tool. mkdtemp looks more appropriate.

If you remove directory in process of working with temporary directory, would 
it help if you create a subdirectory in the temporary directory and work with 
it (including conditionally removing)?

As for the readonly files, was not this problem solved by PR 10320?

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<https://bugs.python.org/issue25024>
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