Luke,
Core Canvas requires Ruby 2.1 as of last week (on master). Ruby 2.2 will be supported soon™ (the last few commits that get tests passing on it should go in this week). As for Rails 5, that is a significantly larger task. Currently, Canvas will boot under Rails 4.0, but is pretty broken, and we haven't even attempted running our test suite against it yet. We will not be jumping straight to Rails 5, as there are many things in Rails 4.1 that are deprecated in 4.0, and completely gone in 4.1 (and same with 4.2), that have no easy backwards-compatibility with Rails 3.2 (since we need to be able to run both versions of Rails on the same code base). So the plan is to get to 4.0, then quick jumps from there to 4.1, 4.2, and possibly 5.0 if it's released by then. This is similar to how long it took us to get from Ruby 1.9 to Ruby 2.1, and now we're already in striking distance of Ruby 2.2. Due to other commitments here at Instructure, we hope to pick up on the Rails 4 work in mid-August or so.
If you and your team would like to expedite the process, you'll need to work within that flow (going to Rails 4.0 first, while keeping Rails 3.2 working). The best thing would probably be to just start running Canvas under Rails 4 (by creating a file `config/RAILS4`), and start clicking around, or running small pieces of the test suite and playing whack-a-mole as you find issues, then sending pull requests for each fix against the master branch. Remember that Instructure has several more plugins that need to keep working, so we'll need to work on those privately, and sometimes they may cause issues with fixes in Canvas core.
Cody Cutrer
Software Engineer
Instructure