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Re:I Used Arch, BTW: macOS, Day 1 by shakna on Saturday July 19, 2025 @09:54PM (#44621218)
It's been five years for my data point, but every single time it came time to update brew, I hit something else I'd never seen before. Every time, it broke.

And from what I can see, migrations are still causing issues. [0]

[0] https://github.com/Homebrew/brew/issues/19951

Re:I Used Arch, BTW: macOS, Day 1 by rob on Saturday July 19, 2025 @10:07PM (#44621293)
Crazy, what kind of set up were you trying to do there? Been using it for probably 10 years and I can't remember the last time I had an issue and I run updates on it automatically every day. Biggest problem I remember is having to chown a directory again or something.
Re:I Used Arch, BTW: macOS, Day 1 by shakna on Saturday July 19, 2025 @10:43PM (#44621520)
It usually hit, when a dependency of programs gets shoved out into cask. The moment where that happens, and where the things listing it as a dependency realise its now cask and not the main repo, is not altogether in sync.