DragonRuby.exe is marked as a Windows application, so double-clicking it won't generate a terminal window. The downside is this means that stdout gets lost even when launched from cmd.exe (dragonruby-publish is marked as a console app, which is why it works there.) This is a quirk of Windows. I'm making a card on our TODO board to find a better solution to this. DragonRuby already does a few minor things differently when it thinks you're developing a game vs playing a published game, so there's no reason we can't make a separate window in the developing case, too. Stay tuned, we'll come up with something!