Forum member nate8nate found out that the Zune HD’s closed ecosystem might be not so closed after all. By installing Windows 7 Phone Connector for OS X and enabling the Zune via commandline he managed to successfully connect to his Mac, and transfer files to the player.
Let’s see how long it takes until that awesome undocumented feature dangerous bug is removed, for your own safety and convenience. Or maybe it’s a sign that Microsoft is loosening its iron grip on their walled garden a bit. Well, that was enough metaphor abuse for one day. Either way, rumors about Zune HD support for Mac have been around for quite a while already – of course support for Zune Marketplace on Mac is a whole other issue.
Check out the full instructions in the forum thread.