[aptwebapps]

Maybe the experience depends on what packages you install?

[microtonal]

It is hard to say, because the grandparent says that Homebrew barely works without providing any examples of the problems they have ran into.

[nickbauman]

Yeah as long as you're using what everyone else is using and stay "inside the lines" it's OK. But step off into special territory, you're better off on Linux.

[natch]

Wild guess: people who keep Xcode and its associated command line tools up to date have smooth experiences. Those who don't, do not.

[wyager]

Brew recently started refusing to install anything if your xcode is out of date, and forces you to wait for a "brew update" if it hasn't updated in 24 hours. It's actually hideously user-unfriendly, but it probably saves the devs a lot of stupid github issues.

[vetinari]

Unless you made the mistake of upgrading to Xcode 8 while staying with El Capitan and then wondering, why nothing works.

[natch]

What specifically doesn't work?

It's working for me but I would love to have an example of breakage to take to my IT as another reason they should allow the company machines to be updated.