[dragonwriter]

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.)

[macintux]

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.

[dragonwriter]

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.