Bested by the beast! After a few days of fighting my Windows demon, I alas leave a bitter and broken warrior. I was able to move the ball a little further forward. I determined that the issues wasn’t actually in the Ruby build scripts but seemed to be related to the way our build scripts were expecting Ruby to be built. Now, it remains to be seen whether that the system works as a whole (Rake was still not installed properly), but I’ve had to switch gears back to working with Elixir.