Look at the pip issue history.

most recently (october?) they vendored some package that was a system dependency before, and it broke the vendored versions of pip (eg. on debian).

I get, “not their fault” debian goes and modifies packages... but from a user perspective: it broke.

I would say my experience is roughly on every six months something to do with pip breaks for me... but I really cant be bothered trying to keep track of it.

I just try to avoid using it now. Down vote all you like, I don't care. Pip has broken my CI enough times its lost any good will it ever had with me.

> and it broke the vendored versions of pip

Wait, Debian updated their pip, breaking it in the process without noticing?

it mostly breaks CIs or docker builds if you don't hardwire the pip version, because they tend to use latest pip by default..., It's mostly not directly pip's fault, but it can get annoying.

I remember issues when they changed their caching mechanism, or when a couple of libraries I was using were importing internal stuff from pip which got changed in a new version.

Also some packages for some reason need to be installed in the correct order and it's not immediately clear until pip tweaks their installation procedure.

I remember in an interview a developer had asked me to resolve the very same problem. And, I actually at the time never heard of it. He said to me that he knew I didn't have a lot of experience using Docker.