Purchased item not playing on Ipod

Question

I hope someone can help me out here, none of my 171 files that I have purchased from the Itunes store are playing on my Ipod, they just skip past. I have tried restoring, deauthorizing and authorizing again, I have also tried uninstalling and reinstalling Itunes, along with rebuilding the library. Any help would be welcome I have spent alot of money on my purchases and they have just stopped playing.

Answer 1

Welcome to Apple Discussions!
Try the steps listed here...
iPod does not play content purchased from the iTunes Store
If the problem persists...
Part 1:
1. Navigate to \iPod_Control\iTunes on the iPod in Windows Explorer. You may have to turn on Show Hidden Files and folders. To do this, go to Tools-->Folder Options, click the view tab, click the bubble to show hidden files and folders, click Apply, and click OK. Look for the presence there of a file named iEKInfo. Is it there? If so, make a copy of this onto your computer somewhere. While there, make a copy of iTunesDB also. Don't delete these copies.
2. Create a new, administrator user in Windows . (Start-->control panel-->user accounts-->create a new account)
3. Log out of the current user.
4. Log into the new user.
5. Restore the iPod as documented in this article:
http://docs.info.apple.com/article.html?artnum=60983.
6. Open iTunes.
7. Set the Music sync preference in iTunes for the iPod to Manual mode.
8. Download the free single of the week from the iTunes Music Store.
9. Verify that the song plays in iTunes.
10. Drag only this song to the iPod.
11. Eject the iPod from iTunes.
12. Disconnect the iPod from the computer.
Does the song play?
If the iPod is able to play this song, follow these steps:
Part 2:
1. Log out of the new user.
2. Log back into the original (affected) user.
3. Reconnect the iPod to the computer.
4. Drag some of the older purchased content (that would not play before) to the iPod.
5. Eject the iPod from iTunes.
6. Disconnect the iPod from the computer.
Does the affected content play?
Is the iPod still having the same issue? Try these possible solutions:
Part 3:
* Delete the SC Info.sidb file as documented in http://docs.info.apple.com/article.html?artnum=302386.
* If the issue persists, recreate the iTunes Music Library as described in http://docs.info.apple.com/article.html?artnum=93313.
Does the music play?
Please post back if this works or not.
btabz