Q: While syncing my iPhone when I was trying to transfer all of my purchases to my computer, iTunes froze up halfway through so I had to manually shut it down and I lost my audiobook that I had just purchased that day. Is there any way to retrieve that when it’s not showing up on my iPhone or iTunes? I have the new iPhone 4S.
A: Unfortunately, the only way to deal with this is to contact iTunes Store Customer Service. The easiest way to go about doing this is to find the item in your purchase history and use the “Report a Problem” link. You can access your iTunes Store purchase history directly through the iTunes Store within the iTunes application by selecting the “Account” link from the Quick Links in the top-right corner of the iTunes Store home page, logging in with your Apple ID and password and then selecting the Purchase History option from your Account Information Page.
In the Purchase History section, click the “Report a Problem” button that appears at the bottom of the list and the click the “Report a Problem” link beside the specific item in your order that did not download properly. You will then be taken to a form where you can choose the problem from a drop-down list and fill in any more information that is required.
This sends a request to the iTunes Store customer service group and you should receive a response via e-mail within a day or two, likely indicating that they’ve simply added the item back to your queue for re-downloading.
Note that if you have this problem with content that is normally available from iTunes in the CLoud, such as music or TV shows (in the U.S.), you can simply go to your Purchased items from the Quick Links at the top-right corner of the iTunes Store and re-download it directly from there. Unfortunately, Audiobooks are not included in iTunes in the Cloud yet.