Purchased music on a second-hand iPod

Q: I recently purchased a 30GB iPod photo from a friend. He deleted all of his music off of it in iTunes, and I put my 20GB of my iTunes on it. The problem is that it won’t play any of the 50 or so songs that I purchased from the iTunes Music Store. What is the problem?

– Andre

A: Problems like this can be caused by one of the following two problems:

  • The iPod is using Manual synchronization mode, and your iPod was never properly associated with your computer.
  • The iPod’s internal software (or “Firmware”) is out of date, and is not able to play recently-purchased music. In April of 2004, Apple debuted an iTunes/iPod software update that “broke” purchased music, requiring users to update both iTunes and their iPods simultaneously. It’s possible that the purchased music is using this updated version of the Digital Rights Management (DRM), while the iPod Software is only equipped for the former version.

In your specific case, the first problem is almost sure to be the culprit, as all iPod photos were produced after the tweak to iTunes’ DRM made with the release of iTunes 4.5.

To fix it, enable “Automatic” synchronization mode, (even if only temporarily) in order to properly associate the iPod with your computer and its iTunes authorization. (More about iPod Synchronization methods can be found here). Apple’s support documentation suggests you may also need to deauthorize (See iTunes’ “Advanced” menu) and reauthorize (play a Music Store track) your computer for your iTunes Music Store account, as well.

If this doesn’t work (and for users who believe they have the second issue), download the latest iPod Software Updater, and use it “Restore” your iPod in order to bring its capabilities up to date, wipe it truly clean, and returning it to “out-of-box” condition for a proper iPod – iTunes setup process.

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