Update: I noticed that which ruby and whereis ruby reports back different locations: which ruby /opt/local/bin/ruby whereis ruby /usr/bin/ruby I recently upgraded ruby to ruby 1.8.7 (2009-06-12 patchlevel 174) [i686-darwin10] and I think I broke rails. When I attempt to load rails. I get an odd message: $ ruby script/server Rails requires RubyGems >= 1.3.2. Please install RubyGems and try again: h