Today, there are two different Ruby implementations on the CLR: IronRuby and QUT's Ruby.Net.
We licensed the Ruby.net codebase earlier this year, and we are using the scanner and parser from Ruby.net in IronRuby today. This helped us bootstrap our efforts, and we know that we have acquired a good scanner and parser that is already highly compliant with MRI:
"In addition to passing all 871 tests in the samples/test.rb installation test suite of Ruby 1.8.2, we are now able to support the standard Ruby test unit library and pass most of the 1864 assertions in the test/ruby test directory."
IronRuby is effectively a continuation of the excellent work that Wayne Kelly, his students, and John Gough have been doing with Ruby .Net. Of course, IronRuby also builds on top of the excellent type system, hosting interfaces, and runtime library work in the Dynamic Language Runtime.
Update:In the comments, Charlie Nutter pointed out that the conformance numbers really only apply if we're using the Ruby.net runtime components. Strictly speaking, that's true. But the real issue here is that we do have a highly conformant codebase that we can look at to help guide us in our DLR-based implementation. I hope this helps to clarify things.