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Presumably actually:

  python -m pip install --upgrade pip
just:

  pip install --upgrade pip
Is “break pip if there is a newer version available”, at least last I checked. (It uninstalls the existing pip but can’t complete the install of the new one.)



I’ve used the latter several times a month over the last year or so, but only since about pip 19.x, didn’t use Python much before a couple of years ago.


It may only be older pip, or windows, or a combination. I've broken pip in quite a few venvs that way in the past though.




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