It Was Bound to Happen Sooner or Later

A couple of years ago, I downloaded The Waifs’ great cover of Dylan’s “Don’t Think Twice, It’s All Right” from the iTunes store. I’ve bought less than five songs from iTunes, so I suspect this was one of their free weekly downloads.

When I acquire a song from iTunes, I usually convert it to MP3 format, and delete the iTunes file. I did convert this song, but didn’t delete the original.

This song came around in the big, randomized playlist on my newish MacBook, and I got the dreaded digital rights management-powered message. This is the first one of these I’ve seen from iTunes (click for a readable version):

DRM Surprise

Let’s see…those five machines would be my Windows desktop, an iMac at the office, our two old laptops and Julie’s MacBook.

It’s no skin off my nose, because I already converted the file to MP3. Interestingly, I only have access to one of those five machines anymore. I could only de-authorize one, therefore extending this file’s life by only one machine.

From the error message, it looks like the authorization is account-wide, not song-by-song. Does anybody know if that’s the case?

In any case, this is pretty complicated stuff for Nomal Human computer users, and it’s a cautionary tale for iTunes song owners. If you forget to de-authorize your old machines, I think you’re limiting your music library’s lifespan. Do I have that right?

UPDATE: Thanks to Dan, who points me to this article describing how to deauthorize all your iTunes-enabled machines from your iTunes account settings. It worked like a charm.


  1. yeah, this just happened to me too. i remember reading somewhere that it’s possible to get Apple to de-authorize some old ones for you, but who knows if it’s true… I definitely haven’t found a way to do it or speak to them about it.

  2. You shouldn’t authorize computers on the same LAN anyways, such as a home network. You can enable sharing in iTunes and other users will be able to access the songs through their own iTunes.

  3. I kinda like to dodge this whole issue by sticking with MP3 format music files. I know AAC files offer better compression, but I favor the universal compatability of MP3 files. They work just fine on my iPod Nano and they also play on a number of other devices – including my TiVo!

  4. Viva the Piratocracy!

    Mme Metro signed up for Napster on a card we got for Christmas that promises “Unlimited Free Downloads!”

    As Tom Waites says “the large print giveth and the small print taketh away.”

    In order for this crap membership to work, Mme had to install Napster software on her machine, and both her portable devices. Spyware? I can’t tell. But I wouldn’t have it on mine.

    The “unlimited downloads” were restricted to a paltry proportion of the available content–excluding the poetry and audio books Mme most desired.

    After three months, the files became unplayable, apparently this is supposed to happen.

    So: For $35 they’ll lend me a few of their thousands of songs to play on devices they authorise, for three months?

    Meanwhile I have no idea what the software Mme had to install could be doing. I don’t even know whether she bothered to uninstall it.

    Personally, I’ll stick with Limewire if it’s all the same to Napster. Or even if it isn’t.

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