pip is too pushy about upgrading, and prompts at inappropriate times

[matt-land]

pip versions less than 10.0 are prompting users to upgrade on every use. In yellow text, on every pip call:

You are using pip version 9.0.3, however version 10.0.1 is available.
You should consider upgrading via the 'pip install --upgrade pip' command.

In this case, the severity is minor. Maybe not the best though. 9.0.3 (the old version) was released less than 60 days ago. Maybe the user isn't allowed to upgrade. Maybe they are in an EDU setting learning python, and every time they use pip, it tells them, hey, why haven't you fixed me yet?

But I want to call out a case where it isn't. When its misleading and confusing to the user.

Stack exchange (real user):
https://stackoverflow.com/questions/49544320/airflow-initdb-failed-importerror-no-module-named-log-logging-mixin

Summary:

• User tries to install package with pip
• Installation fails with a stack trace, an Exception, and is immediately followed by an upgrade warning
• User mis-interprets pip's upgrade warning in the output as being partial cause of the Exception

This seems like a very relatable new user problem.
Many command line tools (aws cli comes to mind) recommend pip as the preferred way to install 'complete working software.' So a pip user is not always python user that can follow the format of a stack trace. Its also a leap to assume any python user can split the structure of stack trace from the install warning, when presenting as a wall of text.

Maybe the solution is to make it more clear to the user that there are two things going on:

• your install failed
• and also, you might want to upgrade this tool

[pradyunsg]

Fair enough.

FWIW, the upgrade message UX can use some improvements. Maybe putting it in a distinct manner (like npm does with a box) has it's merits?

[merwok]

I don’t see merit in making the annoying message more prominent :D

[njsmith]

Unfortunately the annoying message does have to be annoying, because people not upgrading pip is a major blocker on packaging improvements in general. If some people ignore it then it's fine, but if lots of people ignore it then it causes problems for everybody.

No reason it couldn't be clearer, though.

[pradyunsg]

Moved to pypa/pip#5420. :)