I just upgraded to Leopard on my Mac. Previously, on Tiger, I had installed Ruby from source, in the default /usr/local/lib prefix. After reading the discussion on the Apple-provided Ruby installation, I decided to try it – mainly to ensure that my apps, such as GemInstaller, play well with it (on Pivotal’s Mac pair workstations, we still install Ruby from source, so everything matches our demo/production environments as closely as possible, and things are in consistent locations).

So, I wanted to uninstall the old Ruby source installation, and only have the Apple-provided Ruby on disk. Googling for a few minutes did not provide exact instructions for this, so I’m writing up what I did, in hopes that it will help you!

I didn’t use the “–prefix” option when I originally installed Ruby from source, so it was in the default location of /usr/local/lib/ruby, with binaries in /usr/local/bin.

WARNING: Use ‘rm -rf’ at your own risk – a sleep-deprived encounter with ‘rm -rf’ and a stray file named ‘~’ is what “motivated” my Leopard upgrade in the first place…

First, I deleted the old ruby libraries/gems, which was easy enough, because they all lived under /usr/local/bin/ruby:

sudo rm -rf /usr/local/lib/ruby

However, this left all the old ruby/gems executables in /usr/local/bin. This resulted in errors when trying to run executable gems that I had not yet installed under the Apple Ruby installation:

$ cheat
/usr/local/bin/cheat:9:in `require': no such file to load -- rubygems (LoadError)
from /usr/local/bin/cheat:9

Instead of a cryptic rubygems error, I should get a ‘file not found error’:

$ sudo rm /usr/local/bin/cheat
$ cheat
-bash: /usr/local/bin/cheat: No such file or directory

So, I want to purge everything ruby-releated from my /usr/local/bin folder. I whipped up a quick ruby one-liner which just prints out (almost) all ruby-related files in /usr/local/bin:

ruby -e "old_ruby_execs = `egrep 'rubygems|bin/ruby|env ruby' /usr/local/bin/*`; require 'pp'; pp old_ruby_execs.split("n").collect{|line| line.split(':').first}.uniq"

Yeah, I know, ugly and obtuse, but one-liners are kind of fun, and help me remember that Ruby is great tool for sysadmin scripts. Feel free to put it in a class and test it if you are so inclined.

Even though I tried to make a fairly specific regexp for egrep, when inspecting that list, I did find a ‘jgem’ file, which was part of JRuby. I’m planning on reinstalling JRuby anyway, so I didn’t care if that got deleted along with the other ruby stuff.

Anyway, if the output of that looks like everything you want to delete, then run this one-liner to do the actual deed (the ‘sudo echo’ is to ‘prime’ the sudo auth, so you don’t get a noninteractive password prompt):

sudo echo; ruby -e "old_ruby_execs = `egrep 'rubygems|bin/ruby|env ruby' /usr/local/bin/*`; old_ruby_execs.split("n").collect{|line| line.split(':').first}.uniq.each { |exec| p 'removing ' + exec; `sudo rm #{exec}`}"

After that, the only thing that I saw left was the ‘ruby’ executable itself, which I whacked as well:

$ sudo rm /usr/local/bin/ruby

That seems to be about it, as least good enough to get all the old invalid executables off my path. I’m sure this could have been done cleaner if I had taken more care with the original source install. However, a good brute-force approach never hurt anyone. Much. Feel free to post links to relevant and helpful stuff.