Nothing happens when starting "Debug" of Ruby project Follow

Debugging on our remote Vagrant Ruby SDK works okay on our Macs, but my colleague on a Windows machine is having trouble. He cannot seem to start a Rails debugging sesion. He can select the Rails configuration, but when he clicks on "Debug", literally nothing happens. It doesn't seem to register that he's doing anything. Is ther a log we can see somewhere that would tell us where to begin looking for the problem? If the debug window appeared, or a console appeared with an error, it would be great, but we can't even get that far. Any help would be appreciated.