I purchased an audio book on my iPhone 3GS and synched with iTunes on OSX but the audio book didn't transfer to my iTunes. I tried to drag and drop and copy and paste, but iTunes won't let me move the audio book. This is my first purchase through iTunes on my iPhone, but have previously purchased many apps on my iPhone and they always synch to my iTunes.

Any ideas?

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hmm, do u see the same thing with songs purchased on the iphone? – CVertex Mar 3 '10 at 4:13
Do you have the iPhone set to manual sync of songs/videos? What about the tab that would cover syncing of audiobooks - is it set to sync all or selected books? – mindless.panda Mar 3 '10 at 15:36
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4 Answers

Audiobooks are handled under the “music” tab in iTunes. You can do this in a variety of ways. For instance, create a playlist with only the audiobooks you want to sync. Choose the audiobooks from the “Artists” selection in the Music tab. In the summary tab, you can choose to “Sync only checked songs and videos.” Or, you can choose to “Manually Manage Music and Videos” in the summery tab as well.
iPhone to Mac Transfer can fast transfer, rip, copy and manage your Music, Movie, Photo, ePub, PDF, Audiobook, Voice Memo, Camera roll (iOS 4 above), Ringtone, Podcast, TV Show, SMS, Contact, Call List from iPhone to Mac, iPhone 3G to Mac, iPhone 3GS to Mac, iPhone 4 to Mac and iPhone to iTunes.

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I just found out how to do it. Just right click on purchased and select transfer purchased items to itunes. No idea why it doesn't do it automatically like apps, but it is done now.

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I was looking for this exact thing, and it seems they have changed iTunes a little since this was posted. Fortunately it put me on the right track. In iTunes 10 what you have to do is plug in your iPhone and when it shows up in the left pane in iTunes, highlight it, then right click and select "Transfer Purchases". At that point you don't have to sync or anything to get them to move, they just start transferring! It's annoying that Apple doesn't make information like this readily available. Thanks for sharing your discoveries! ~Adam

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Purchases made on your phone should be automatically synced back to iTunes. Be sure that you don't have a 'Source' hidden from the GUI and that's why you can't find it (check preferences). If all else fails, and you can verify that the audiobook is on the phone, use Senuti (iTunes spelled backwards), an app for copying files off your iPod without iTunes: http://www.fadingred.com/senuti/

This should at least let you dump all of the files to a temporary location (i.e. a folder on your desktop, etc) and then put it into your iTunes library 'manually'. Just resync and get your iPhone back the way you want it and go from there.

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