I think I just saw another message indicating there was something dramatically wrong with this release.
I also strongly believe that pip should not be the stick to encourage people to leave Python 3.4 or 2.7 behind. To be clear, I am fine with newer versions of pip not supporting older versions of Python – however, pip tends to aggressively encourage upgrading, and this can leave users with two bad options: they can either not upgrade pip and live forever with its misguided warnings, or they can upgrade pip and risk being broken, with no easy way to back out of this situation.
I think it would be better if for each Python version that reaches its EOL, there was a final pip release supporting that Python version that did not emit any warnings suggesting an upgrade (neither of pip nor of Python).
Presumably users who don’t upgrade their Python version have made that choice understanding the consequences – and if they don’t, I doubt a warning from pip will sway them. This is especially true for Python 2.7: few folks are willingly staying there, but for some of us the migration will still take years. I don’t mind not being able to upgrade pip or not being able to use newer pip features – but I do mind getting non-actionable warnings every time I use pip, and I am not looking forward to the day when pip stops working because some part of the PyPI infrastructure stops supporting pip running on Python 2.7.