RubyGems Missing, frustation with Solaris CoolStack and Jruby

I'm having growing doubts about Solaris Coolstack tomcat, it has a lot of weird timing issues with Jruby. Were seeing an issue where 'sometimes' when you startup tomcat it will give you this error : Rails requires RubyGems >= . Please install RubyGems and try again: http://rubygems.rubyforge.org . Without changing any configs or anything in the exploded war, I can start the server and sometimes it works and sometimes it won't start. I even tried to move the jruby-complete jar into Tomcat's common/lib folder so it would get loaded before rack. Is there any way that the core Jruby included files like rubygems isn't getting loaded before Rack loads up the boot.rb ?