Unable to load an audiobook on a ipod classic 5 gen

I just purchased a used ipod classic 5 gen. After resetting the ipod as noted on itunes, I went to sync an audio book to the ipod and get an error message that the audiobook was uinable to be loaded on ipod. What am I doing wrong?

Try:
- iOS: Not responding or does not turn on
- Also try DFU mode after try recovery mode
How to put iPod touch / iPhone into DFU mode « Karthik's scribblings
- If not successful and you can't fully turn the iOS device fully off, let the battery fully drain. After charging for an least an hour try the above again.
- If still not successful that usually indicates a hardware problem and an appointment at the Genius Bar of an Apple store is in order.
Apple Retail Store - Genius Bar

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Regards. T

Do you have a 4th gen iPod or an iPod Classic? They're not the same and the instructions will be different.
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Connect device to iTunes, select the device either from the device icon at the top-right or from the sidebar (enable with CTRL+S), select the Books tab, then scroll down for options to make sure the book is selected to sync, and sync.
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Has a fix for the audiobook problem on ipod classic been released yet?

My fiance just gave me an ipod classic 160g for valentines day. I turned it on and uploaded my large collection of audiobooks just to find out that it throws them all into a pool of chapters. Is this something I am doing wrong or has apple still not published a fix for this? A bit of searching shows that several users have faced the same frustration.

Check some of the audiobooks in your iTunes Library. Use File/Get Info/Info. Are the basic fields completed, such as the Track Number and total tracks, the Disc Number and total number of discs. Without that information, the iPod will have difficulty in sorting them into the correct order.

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See Audiobooks on iPods.
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I recently bought an ipod classic, but it will not sync my purchased movie. I've noticed the movie has an exclamation mark beside it. When I checked my itunes file; the movie downloaded to a "Downloads Folder", is there something wrong?

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Thank you so much! It's updating now. I'm hoping that once the update is finished that it will sync like normal as well. Of course I'm still a bit confused/concerned about how it refused to update on it's own, but for now that's not a problem. Hopefully from now on there won't be any more problems.

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This forum is for troubleshooting Apple Software Update for Windows, a software package for Windows designed to update Apple products that run on Windows, and not related to iPods or iTun es
You should consider posting your question in the iPod and/or iTunes forums:
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http://discussions.apple.com/category.jspa?categoryID=151

I have tried syncing an audiobook to my Ipod Classic 160GB...

...but it refuses to transfer from my Library! I have tried restarting my computer, restarting my Ipod, unplugging it and plugging it back in, resetting my Ipod - you name it. I have tried manually dragging the book file from my desktop to my Ipod icon in iTunes, but still nothing, and it has that crossed-out zero logo with it when I try to move it. It is in my Library, like I said, but just won't move to my device. Any suggestions you have would be most appreciated.

It sounds like your iPod is set up to automatically sync content from iTunes. And if that is the case, you'll want to double check to make sure your iPod is set up to sync audiobooks from under the iPod's Books configuration tab/pane in iTunes.
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Unable to load an audiobook on a ipod classic 5 gen

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