It seems Rails is preventing autoload by removing the gem's load path from $:. I see two available options:

1. load everything in advance
2. set up autloading with absolute paths

I don't want to go 1. because autloading saves memory and time, especially when running CodeRay from the command line.

A version of 2. is in the above commit, in the autoload-fix branch. It fixes the pry issue on my system, but it's defining a Module#coderay_autoload method to do this. Any ideas how to avoid this?

Perhaps we can use autoloading just for the executable version; it seems it's not a good idea to use autoload in libraries.