Jiva,
It's complicated. I started using Ruby years ago with SketchUp. Been away from SketchUp for while, but I'm still using Ruby.
As I recall, the files get split into two locations, you have to edit the SketchUp.exe file, etc.
I've also been building Ruby for quite a while, so the files I used were my own and built with current compilers & toolchains. With SU 2017, it can only run with Ruby 2.3 due to the changes that occurred in Ruby 2.4.
There may be a publicly available build of Ruby 2.3 in the (hopefully near) future...