Cannot play .m4p songs on iPod

You need to play at least a part of songs purchased from the iTMS to authorize them. They won't copy to your iPod until you do this.
How to transfer Purchased Music from iTunes to your iPod
iTMS Song and Computer Authorization

If you've played & authorized them in iTunes and they still skip, try this. De-authorize the computer in iTunes/Advanced menu, then re-authorize it. You re-authorize it by playing one of the songs purchased from the iTunes Music Store within iTunes. It should ask you for your Apple ID and password, and then the computer will be authorized again. Sync your iPod with iTunes, and those songs should play on the iPod once again.

Another common cause of this is not having the latest version of iTunes.

If you are using the latest version of iTunes (6.0.4), then you need to make sure your iPod software is up to date also. Get the iPod Updater software, install it, run it and update your iPod.

When you have done this, authorize your music in iTunes by playing a few seconds of it within iTunes, re-sync your iPod, and it should transfer by whatever synching method you choose.

If you have made sure that both the iTunes and iPod software are current and have deauthorized and reauthorized your computer, try this test:

1. Deauthorize the computer.
2. Create a new user in the system.
3. Download the free song of the week from the iTMS in the new user account.
4. Play the song in that user account to authorize again.
5. Restore the iPod (using the iPod updater) in the new user account.
6. Sync just the free song of the week and see if it plays on the iPod.

If it does, you appear to have a corrupted iTunes library file, and you should recreate the iTunes library file in your normal user account, and then sync your music back to the iPod and all should be well.

The following articles will help you.

Authorization and Deauthorization.

How to create a new user account in Windows.

How to restore the iPod.

How to recreate your iTunes library.

Hi

I'm having the exact same probelm with m4p files that I've purchased from iTunes.

I've followed all the advice you've posted here (latest iTunes and iPod software, authorize/deauthorize, etc) and still these tracks just skip when I reimport them and sync my iPod (20Gb Photo, 4th gen).

Really doing my nut in, as I can't listen to purchased tracks on the go! Any more suggestions?

Thanks.

I have the exact same issue and have tried all variations of fixes posted to no avail. This is my first experience of using ITMS and it *****...

You cannot download your music a second time either, yet the support incident that I logged states that I must have corrupt files.

ARRRGGGGHH

Anybody who has had this problem and fixed it please reply, I have spent most the day training the net and this seems to be a common problem.

I have a 5 gen iPod and want to send it back already.

Thanks in advance

5 gen iPod Windows XP Pro SP2

Got that nasty problem too. All protected M4Ps purchased at the ITMS play fine on the computer, but continuosly skipped on my iPod Nano 4G.

Spent two days doing all that stuff, 5Rs, re-installing, resetting, reformatting, deauthorizing/authorizing. No luck. Protected M4Ps won't play on iPod Nano and simply skipped. Though other protected files purchased at audible.com for example, play ok on the iPod.

It's my first experience with the ITMS and so far it, sort of, ***** 🙂

Sent a request today to the ITMS support team, let see what they'll say...

Some updates on the problem http://discussions.apple.com/thread.jspa?threadID=463127&tstart=0&messageID=2415 723#2415723

There ya go!