A few weeks ago, my laptop’s screen gave out. I switched to a new laptop, and used Apple’s handy-dandy migration assistant, which worked well for everything except my development environment.

The first sign of trouble was when I tried to run bundle and got

/usr/local/bin/bundle: /usr/local/opt/ruby/bin/ruby: bad interpreter: No such
file or directory

…what? I tried reinstalling Homebrew’s ruby, which didn’t work.

When I ran brew upgrade, many packages could not be built because it could not find dependencies in /usr/local/opt (double what?). I started individually re-installing packages (via brew unlink and brew link, but realized that most of the errors laid in a bunch of files in /usr/local/share. Luckily, anything in usr/local is not critical to the OS, so you can remove files (at the risk of reinstalling missing dependencies, which I was doing anyways).

I ended up doing this to fix my troubles:

  • Empty /usr/local/share
  • Run brew update && brew upgrade
  • Run brew list | xargs brew reinstall
  • For good measure, run brew doctor and fix what it complains about.
  • I also started using rbenv. Even though I never use ruby, it’s nice (I can run jekyll without prepending bundle!)
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