Knowledgebase: iPhones and iPods
Tracks from the iTunes store don't play on my iPod
Updated by Russell Samuels on May 26, 2008
Tracks that are purchased from the iTunes store are often protected
with DRM (digital rights management) protection that limits the tracks'
ability to be played, copied, or converted. Such tracks are usually
.m4p and sometimes .m4b files.

MediaMonkey can sync such files to an iPod, however, for the iPod to
be able to play the tracks, the iPod must first be granted rights to the
tracks by 'registering' with the copy of iTunes that has rights to the
tracks. This 'registration' can be accomplished via either of the following:
1) When the iPod is connected to the PC for the first time while iTunes
is running, use the 'Register my iPod' function from the
iPod Setup Assistant).
2) Sync protected content to the iPod using iTunes. This is easiest in
most cases:
1) Run iTunes
2) Plug in your device (make sure that iTunes is configured to NOT
sync automatically)
3) Right-click on your iPod/iPhone and click 'Transfer purchases'
4) Close iTunes

Any iTunes DRMed tracks subsequently synced with MediaMonkey
should play successfully on the iPod.
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