I used this briefly in an internship as part of a build system. Most
problems we had were down to windows using \ rather than / in its
paths.
Pickle has these hard coded in its require statements. I don't know if
Ruby is smart enough to fix these natively, but I think File /
FileUtils class has some bits that will help if it doesn't.
That said wouldn't the requires be blowing up if that were the issue?