Try this and see if it works for you.
I had some issues with my iTunes-managed music collection after I installed the new drive. Some tracks refused to play, so I have to assume the DRM mechanism does some hardware testing on more than just the logic board.
What I have found is that the DRM on some files is not as airtight as on others, reflecting when/what version of iTunes/the music store was in use when purchased. Specifically, if you select a protected AAC file and choose “Convert Selection to [MP3|AAC|Lossless|AIFF|WAV]”, whatever you have in your prefs, you may be able to do just that: you’ll end up with an unlocked file. It works for some files, but not for others, so I assume this is one area where the arms race has gone our way.
So here are two screengrabs of a before and after. This is the DRM-encumbered file.
And this is the liberated one:
It looks like the DRM imposed by older versions of iTunes (4.6? Yikes) can be cracked by newer versions. I successfully liberated 92 tracks and have still more to examine. It looks like a crucial window in Dec 2005 was open for a short time: I don’t think I was using iTunes 4, more like 6, but perhaps the DRM engine was out of sync on one end of the transaction
This really just underscores how wasteful the DRM battle is. It’s an arms race, as many have called it, and no one wins. The people/entities on whose behalf it is being waged — the RIAA cartel — aren’t even paying for it: it’s consumers, software/hardware vendors and artists who pay.
Thanks to my neighbor and fellow DRM opponent for some rigor on this.