Now play a few purchased songs for a few seconds. It will ask for your account information (from the iTunes Music Store). If that doesn't work, in iTunes, go to advanced->deauthorize computer. If not, make sure everything is up to date on your computer. Have you played the songs in iTunes for a few seconds? This will authorize them. These are general troubleshooting steps to take. Should I connect the unit directly to the back of the PC? I then completely erased all data on the iPod and let it restore all songs from iTunes. I downloaded the iPod updater 3/23/06 and upgraded my software to from 1.1 to 1.1.1 but that did not solve the issue. It does this until it goes though all 134 tunes I have on my iPod. Then it plays that song just fine, completes, goes to the next and again, if it is a downloaded tune, it does the same thing. It then shuffles to another tune and if it is a downloaded tune, it displays the album cover and tune information like it is going to play it, but then it just skips onto the next tune, and the next, and the next until it finds another tune from this CD I ripped into iTunes. If I shuffle, it will play a tune from the ripped CD album just fine. Oddly enough, the 1 CD I ripped into iTunes plays just fine on the unit. Now, it will not play ANY downloaded music from iTunes. My iPod was skipping on all downloaded music seemingly at random.
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