While this doesn't help him get his time back, next time I'd encourage him to use rvm as the other posters have previously indicated — but instead of actually i

While this doesn't help him get his time back, next time I'd encourage him to use rvm as the other posters have previously indicated — but instead of actually installing the massive XCode bundle (4GBs is a lot if you're using an SSD) I recommend he check out this 300MB bundle you can install which is just gcc and the other bare minimum tools you'd need to get ruby and the various gems working: https://github.com/kennethreitz/osx-gcc-installer https://github.com/kennethreitz/osx-gcc-installer Also, one small gripe is that it sounds like the majority of his complaints were actually trying to get Python and Mercurial working. This isn't really the fault of OS X nor does it bog down most Rails devs working on OS X. Just some perspective!