iPod Special Report: iTunes-purchased tracks won't transfer to iPod

A growing number of MacFixIt readers are reporting an issue where tracks purchased through the iTunes Music Store do not automatically transfer to an iPod during the on-connect synchronization process.

MacFixIt reader Michael Hammermeister, for instance, writes:

"I just noticed this morning that my iPod would not fill with purchased music from my iTunes library. It fills with my ripped (CD) music but not with purchased. At one point I got a message saying that some songs including (songs that I had purchase through iTunes) because they cannot be played on this iPod. I have for the since buying my iPod Shuffle been able to auto-fill with both purchased and ripped."

There are a few potential solutions to this issue.

First, select one of the purchased tracks and attempt to play it. In many cases, the song will not be authorized for play on its host Mac, and you will be required to enter your Apple identification e-mail address and password. After authorizing the song(s), re-attempt synchronization.

Second, make sure that your iPod's firmware is up-to-date. Download the latest iPod updater.

Finally, failing the above to procedures, try performing a Restore process on your iPod. Note that you will lose all music currently stored on the iPod during this procedure.

• When songs won't play
• Warning about Windows DRM and the iPod
• Using Apple's Disk Utility, other disk tools to solve iPod directory/permissions problems
• USB 2.0 synchronization/data transfer problems
• Audio dropouts, pauses
• Revitalizing a frozen/unresponsive iPod
• Sudden, Unexpected Resets
• Repair difficult, replacement often cheaper: Cracked LCD screens and more
• Quirkiness when synchronizing with high-power USB 1.1 ports
• Mac freezes when going to sleep with iPod connected
• iTunes-purchased tracks won't transfer to iPod
• iTunes crash on iPod connection; solutions
• iSight interference
• Falling Asleep (appearing off) suddenly
• iPod-stored tracks cannot use some iTunes features
• Updater software issues
• Shuffle USB connectivity issues
• Remote Control problems
• iPod not showing up in iTunes
• Batteries: Charging, maintaining capacity, maximizing life; more
• Preferences not sticking
• Extracting files from an iPod to a Mac
• Distorted/static sound
• Dealing with Smart Playlists
• AppleCare for iPods
• Complaints about Apple earbud quality; alternatives
• Data loss -- Music disappears from iPod

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