Chris Tse <chris...@hey.com> added the comment:

UPDATE:

After some further investigation, it seems like even on cmd and seeing the 
(myenv) indicator, it actually seems to be falling back to system pip and 
installing packages globally. Running `.\myenv\Scripts\pip.exe` actually throws 
that same error. CMD just seems to fallback to system pip and silently fails 
the desired venv pip, unlike Powershell.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue41925>
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