Q: Is there a way to recover music that you have purchased that has been synced to a device after moving to a new Mac? I know you can have up to 5 machines. But there is no way to backwards sync my music to the new Mac. With iTunes plus you would think you would be able to push from a device to a Mac or PC. This will most likely be resolved with iCloud.
A: Actually, you can transfer any content that was purchased from the iTunes Store from your device to a new Mac using a built-in feature that was first introduced back in iTunes 7. You will first need to ensure that the new Mac is authorized for the same iTunes Store account that was originally used to purchase the content. You can do this by going to the Store menu in iTunes, choosing the Authorize This Computer option and entering your iTunes Store Apple ID and password.
If you have content purchased with more than one iTunes Store account, you can simply repeat this process to authorize the other accounts. Once you have done this, connect your device and iTunes should actually prompt you that it has found purchase content on your device that is not on your computer, providing the option to transfer those purchases.
Clicking the “Transfer Purchases” button will copy all of the purchased content on your device that matches any of the iTunes Store accounts that your computer is authorized for. This includes not only music, but also audiobooks, movies, TV shows and even iBooks and iOS applications.
If the dialog box doesn’t appear, you can still initiate the transfer manually by choosing Transfer Purchases from the File menu in iTunes.
Note that this procedure will not transfer content that was not purchased from the iTunes Store. Other content will still need to be transferred back manually using a third-party utility. See Copying Content from your iPod to your Computer for more information.