It’s interesting that pip is installed as a --user package in your profile’s roaming appdata. If you installed Python for all users, pip may have previously opted to do a --user install without getting your consent, which is quite rude. Personally, I never want that. If I mistakenly update an all-users installation of pip from a shell that lacks admin access, I immediately uninstall it via py [-X.Y] -m pip uninstall pip. Then I open an administrator shell and do a proper upgrade of the system installation of pip.
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