I'm working off these instructions: http://github.com/dcparker/ruby-gmail From the home directory I do a standard install and good stuff happens: Johnny-Goodmans-MacBook-Pro:gmail johnnygoodman$ sudo gem install ruby-gmail Successfully installed ruby-gmail-0.2.1 1 gem installed Installing ri documentation for ruby-gmail-0.2.1... Installing RDoc documentation for ruby-gmail-0.2.1... I head over to my ~/www dir where I run scripts that include other rubygems successfully and create a gmail directory. I create a script that includes rubygems and gmail, but does nothing else: Johnny-Goodmans-MacBook-Pro:gmail johnnygoodman$ pwd /Users/johnnygoodman/www/gmail Johnny-Goodmans-MacBook-Pro:gmail johnnygoodman$ ls test-send.rb Johnny-Goodmans-MacBook-Pro:gmail johnnygoodman$ cat test-send.rb require 'rubygems' require 'gmail' I run this script and the errors begin: Johnny-Goodmans-MacBook-Pro:gmail johnnygoodman$ ruby test-send.rb /Library/Ruby/Site/1.8/rubygems/custom_require.rb:31:in `gem_original_require': no such file to load -- mime/message (LoadError) from /Library/Ruby/Site/1.8/rubygems/custom_require.rb:31:in `require' from /Library/Ruby/Gems/1.8/gems/ruby-gmail-0.2.1/lib/gmail/message.rb:1 from /Library/Ruby/Site/1.8/rubygems/custom_require.rb:31:in `gem_original_require' from /Library/Ruby/Site/1.8/rubygems/custom_require.rb:31:in `require' from /Library/Ruby/Gems/1.8/gems/ruby-gmail-0.2.1/lib/gmail.rb:168 from /Library/Ruby/Site/1.8/rubygems/custom_require.rb:36:in `gem_original_require' from /Library/Ruby/Site/1.8/rubygems/custom_require.rb:36:in `require' from test-send.rb:2 Johnny-Goodmans-MacBook-Pro:gmail johnnygoodman$ Here's my gem env: Johnny-Goodmans-MacBook-Pro:gmail johnnygoodman$ gem environment RubyGems Environment: - RUBYGEMS VERSION: 1.3.7 - RUBY VERSION: 1.8.7 (2009-06-08 patchlevel 173) [universal-darwin10.0] - INSTALLATION DIRECTORY: /Library/Ruby/Gems/1.8 - RUBY EXECUTABLE: /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/bin/ruby - EXECUTABLE DIRECTORY: /usr/bin - RUBYGEMS PLATFORMS: - ruby - universal-darwin-10 - GEM PATHS: - /Library/Ruby/Gems/1.8 - /Users/johnnygoodman/.gem/ruby/1.8 - /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ruby/gems/1.8 - GEM CONFIGURATION: - :update_sources => true - :verbose => true - :benchmark => false - :backtrace => false - :bulk_threshold => 1000 - :sources => ["http://rubygems.org/", "http://gems.github.com"] - REMOTE SOURCES: - http://rubygems.org/ - http://gems.github.com The path that the errors give when I run the script is not the same as the GEM PATHS given in the env output. However, I don't know how to make them match or if that's the significant thing here.