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My iPod Classic 160 GB, late 2009, has stopped syncing library content (using iTunes ver 10.6.1). The iPod still has 135.8 GB free memory. I have many Audible books in the "Books" library, but only four of them are synced to the iPod. All podcasts, as well as iTunes U, sync OK. My DVDs and converted movies are also affected by this problem - out of 10 movies, only three are synced to the iPod.

Does anyone have any ideas or advice?

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You should not assume that everything you buy at the iTunes store or rip from other sources is going to be playable on the classic iPods. Video iPods have varying playback capabilities and the classic iPods are the least capable. The technical specs at the Apple store will give you the details on what's playable. If the video files won't play on the iPod, iTunes quietly refuses to copy them over. You must buy compatible content or rip to the specs that the iPod demands.

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There may also be a discrepancy between what's in the library and what's n your ipod. What is added to the library may or may not be aded to the ipod, this depends on your settings. To make sure every file is synced that you'd like to sync, you may want to go to your ipod in Itunes, then select the bottom option to manage your library manually. Then, add files by dragging to the ipod directly, rather than through the general library. This is especially useful if your problems are due to changing computers, so that there is a discrepancy between what's on the ipod and what's in the library. Of course, if you have files on the ipod that aren't playable, there is nothing to do about it. But your question seems to suggest that things were OK before and that this is no longer the case now. Trying out manual ipod library management may be helpful then.

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Had trouble sync-ing audible book to my iPod. I could get the book into iTunes but would not synch from there - kept getting error message "…will not play on this iPod." Wasted HOURS online thinking I had to find a file converter from AA to mp3 ...…rip from a virtual CD….so many posts. Dumb. All the posts I read were wrong.

Just download the audible book (from Audible Books in my case) in a different format. Not all iPods are compatible with their standard download type. If you click download from the Audible Books site, the book format is automatically 'enhanced.' Change it to "Format 4". You'll find this drop down option on the Audible Books/library/above the search bar.

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I was getting a few errors with mine. I ran an mp3 validator on my files and found most of them were corrupted from one too many transfers from machine to machine. Try running a validator on your files and repair what can be repaired and see if that helps. I used this one

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