I may have narrowed it down the what the problem is. iTunes is not dealing with DRM restrictions well.
Workarounds first, if you are having sync problems with iTunes 11.1.x:
- Do not try to sync audiobooks with DRM restrictions.
- Use Audible.app to download the books & play them for Audible books.
- Use Overdrive.app to download the books & play books from your library checked out from your public library with Overdrive.
- Do not try to transfer the books with Overdrive Media Console if it fails.
- Books without DRM restrictions will sync with iTunes 11.1.x, IF there are no books with DRM restrictions in the sync.
This will require a bug fix from Apple.
Now, how I came to those conclusions.
iTunes 11.1 & iTunes 11.1.1 are having problems syncing audiobooks to iPhones. I worked with an Apple Senior Advisor and having information sent to their Engineers, for 2 weeks with no resolution or narrowing of the issue.Myself and a several other users have narrowed it down to the DRM restrictions on these books that is causing the problem. I have been following several threads here and elsewhere for weeks.
When I try to sync audiobooks to my iPhone 4S, if there is an Audible audiobook in the sync, it will fail. What happens is that in the next to last step, iTunes hangs and 9 times out of 10, it will self cancel the sync. On the one time it does complete, it will have failed to move the books over to the iPhone. It is even worse on my iPhone 3GS.
If I download a book from the public library with Overdrive and then try to use Overdrive Media Console to transfer the audiobook to iTunes and from there to the iPhone it will fail. The DRM restrictions in OMC are causing the problem during the transfer.
The DRM restrictions that are causing the problems.
I can transfer all the audiobooks I have if there are no DRM restrictions on them, unless there is one with DRM restrictions in the batch to be sync'd.
Brent
MacBook Pro, OS X 10.7.5, iTunes 11.1.1
iPhone 4S, iOS 7.0.2
iPhone 3GS, iOS 6.1.3