Tikkabik

Yep, it's a pain in the ass according to Apple's own Knowledge Base.

When I mused about the iTunes Music Store the other day, I pondered how the three Mac authorization system worked, and that question is more or less spelled out in this new Knowledge Base entry. According to Apple itself, it's advisable to de-authorize your computer before you sell or donate it, implying that the DRM is locked to the actual hardware itself, rather than any three Macs.

That's a real pain in the ass. There should be a more effective way of handling this, because it's something you have to remember to do before you stop using a computer. There are a few worst-case scenarios where this could be a real problem, such as a complete failure on a system, necessitating a motherboard replacement (different serial number) or a complete system replacement.

Or imagine, for example, that you set your home Mac up in your router's DMZ and share your own playlist with your computer at work, authorizing your work computer to play your protected home stuff -- then you get laid off or fired, and you're prevented from de-authorizing that system first.

There are a few other permutations that bother me, too, but that should give you the general idea.

A better way to do this would be to make de-authorization of remote computers possible from the "master" from which the music was purchased to begin with. Right now, as near as I can tell, iTunes doesn't permit this. I wish it did.