Not to pile on, but I thought Homebrew handled the Python2 -> Python3 cutover poorly. A routine `brew upgrade` resulted in python being de-syslinked. For me, this meant a bunch of tasks broke silently in the background. It took a little while to find out that it was just the case that `python3` became the default interpreter and thus I needed to install some dependencies for scripts running in the background.

It's totally fine as my code was python3 compatible, but I was surprised that they'd apply a breaking change like this silently. Unlike OSes which might do this kind of thing with a major version update, I was surprised, and it took me a little while to diagnose what happened.

When I checked the GitHub discussions about the change, I found two things: 1) The maintainers claimed they had given a soft deprecation message a few months prior -- but brew doesn't stop for user input, it just posts walls and walls of messages, so I had naturally tuned it out. 2) The maintainers were getting ballistic mad at people who didn't think this was handled well.

Of course, open source is open source, and maintainers owe us nothing, but I was surprised that such a critical piece of infrastructure was being managed by people who imho handled a potentially non-trivial transition like this and who clearly didn't have the diplomatic tact to handle their userbase.