I've actually found JRuby to be very handy when it comes to packaging. Using warbler I can generate a jar file and then using the javapackager I can create self contained packages for all the major platforms/package managers: windows (.exe/.msi), linux (.rpm, .deb), osx (.dmg). Way more painless than packaging a ruby runtime. I've tried traveling ruby, but have not had the same seamless experience. Especially when it comes to multiple platforms. However, packaging with java, jruby and my application usually turn out to be quite large. Around 80Mb for a CLI and the startup time for short running programs like CLIs using JRuby can be quite long.