Q: My wife’s friend transferred audiobooks from her iPhone 4, using her iTunes account, to my wife’s iPod touch, which is linked to my iTunes account. I am now trying to update the software on her iPod touch, but I keep being told that there are purchases that need to be transferred to my iTunes library. Can you help me?
A: The most likely problem here is that the audiobooks your wife’s friend transferred to the iPod touch were purchased with the friend’s iTunes Store or Audible account. While iTunes can transfer purchased items back from an iPod or iOS device, this only extends to items purchased with accounts for which the current computer is actually authorized.
Your wife’s iPod touch would be authorized to play these items as they were transferred from an authorized computer, however since your computer is not authorized for that iTunes Store account, they won’t be transferred back into your iTunes library.
The only way that you will be able to transfer these purchased audiobooks back into your own iTunes library is to authorize your computer for your wife’s friend’s iTunes Store or Audible account that was used to purchase those particular audiobooks. For an iTunes Store account, this can be done by selecting the Authorize This Computer option from the Store menu in iTunes and then entering the appropriate Apple ID and password.
If the content was purchased with an Audible account, this process is a bit more complicated, as you can only authorized an Audible account when trying to actually play content that was purchased with that account—there is no menu option to access this feature manually. If you select the audiobooks from your wife’s iPod touch from within iTunes and attempt to play them from there, you should see a prompt requesting an Audible username and password in order to authorize your computer for these items.
If you do not have access to the account information that was used to purchase these items, then you will either need to proceed with the update without transferring them back—assuming iTunes allows you to proceed—or manually delete these additional items from the iPod touch before performing the update.
Note that in most cases you should be able to proceed with an iOS update without actually losing any of your purchased items; iTunes merely prompts you to transfer purchased items back to your library as a precaution against problems during the update process.