jt <jonas@thiem.email> added the comment:

> alternatively, you could perform an unattended installation:

I know, I already listed the downsides above. (Basically outside of a container 
it's a bad way to do things because it has too many side effects, and it likes 
to break when interrupted after which you will need to repair/reinstall, then 
uninstall again, only then you can do a clean install... it is quite annoying.) 
It's not that it's not working, it's just not a very good option in some 
scenarios which is why I made the ticket

> That's normal behaviour. You can't upgrade pip in-place with the wrapper

Oh, right! Thanks, that explains it. In that case I suppose it works perfectly 
fine? Does that mean there's a chance venv & ensurepip will be added to the 
NuGet version? Because then I'm definitely switching over to that one for good

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<https://bugs.python.org/issue36010>
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