I originally had a problem when I downloaded an audiobook to my iPad. I wanted to sync it to my iPhone and iMac. I could not locate any method to do so from devices themselves. I connected the iPad to my iMac and proceeded to transfer purchases. The item then disappeared from my iPad and there was no trace on my iMac. I fixed the problem by locating the receipt email Apple had sent for my purchase. I found the item in question and clicked on report a problem, I chose item didn't download or could not be found. It will redirect to your iTunes, go to the Store menu, check for available download, authenticate with your apple crdentials and presto. Hope this helps.