Steve Dower <steve.do...@python.org> added the comment:

Unless someone can find an authoring bug under Tools/msi, I don't think we can 
do anything about this. We rely on the built-in Windows support for adding and 
removing these variables, and if that's broken, we can't do anything with our 
current setup.

I really want to get us out of this addiction to cluttering up PATH with lots 
of different directories - it's bad for security/reliability/etc. of the system 
as a whole, and I don't like Python being the cause of issues here. But I 
haven't quite come up with the better design yet... 

Anyway, all that to say that I'm not in any rush to expand or seriously mess 
with the current PATH settings. If there's an authoring bug we can fix, great, 
but I don't think this one is on us in a way we can easily deal with.

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<https://bugs.python.org/issue45969>
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