Q: I got a new laptop last Christmas and I downloaded iTunes onto it. Now I’m trying to sync my music, pictures, and videos from my old computer to my new laptop, but when ever I click the Sync button for my iPod, two choices pop up: “Erase and Sync” and “Transfer Purchases.” I don’t think I want to erase my iPod so I click Transfer Purchases but all that pops up is an error message which shows all my purchases as an error! What do I do?
A: Firstly, if you still have your old computer available, it would be far simpler to transfer your iTunes library from the old computer over to your new laptop. This would ensure that any ratings, playlists and other metadata are preserved, and since it would be the library database, iTunes would immediately recognize your iPod as already “belonging” to your new laptop and it would sync seamlessly. Check out our tutorial on Transferring your iTunes Library for more information on how to do this.
If you no longer have the old computer, you can recover your content from your iPod back onto your new laptop, but you will likely need a third-party tool to accomplish this. The “Transfer Purchases” option in iTunes will only transfer back music purchased from the iTunes Store, so unless your library consists solely of iTunes-purchased content, you will still need a method for getting your other content transferred back. Our tutorial on Copying Content from your iPod to your Computer provides more information on some of the tools available to do this.
The errors that you are seeing when transferring purchases are likely related to your new computer not having been authorized for the iTunes Store account that was previously used to purchase these items. You can manually authorize the new computer by selecting Store, Authorize Computer from the iTunes menu and entering your iTunes Store user ID and password.
Note that transferring your iTunes library from your old computer is definitely the best of these options if you still have this available, since all of your relevant data is there. Third-party tools which recover content from an iPod attempt to rebuild your iTunes library based on what’s found on the iPod, but this is a less accurate process than simply transferring over an exact copy of your library database in the first place.