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I'm use a Mac and so the directions didn't quite match what I had to do to install games.

  1. Connect the PlayDate to your Mac using the supplied USB cable.
  2. In Finder click on the PLAYDATE drive and navigate to "/Games/User"
  3. There should be a file similar to "user.XXXXXX.com.shadowbreakgames.speccydate.pdx". Right-click on it and select "Show Package Contents"
  4. Copy your game files into the "games" folder.
  5. On your Mac eject the PLAYDATE volume

Fantastic project - just completed the first level of Manic Miner, brilliant! :)