Myself and a coworker ran into an issue that only appears with Lighttpd. It does not happen with Webrick or Apache. Our rails app uses libraries outside the ruby standard library paths, and outside our rails application directory. When trying to add those directories to our load path, it was getting screwed up. Here is my posting of the problem in full and the solution we came up with: http://blog.mktec.com/zdennis/ruby/ror_lighttpd_fastcgi_1.rdoc If anyone else knows of a better way to fix this please let me know. Thanks, Zach