Q: My husband replaced the hard drive in my laptop. However, even though I have songs that I purchased from iTunes in the library of the laptop, there are 55 songs that won’t transfer to my iPod. iTunes says that these items are not authorized to play on my computer. I’ve authorized the laptop but these 55 songs still won’t transfer. I’ve erased and reset my iPod to factory standards and even made sure I’ve enabled my disk use. Any suggestions?
A: You may want to confirm that these songs were purchased with the same iTunes account that you normally use. If you have used different iTunes Store accounts in the past, then each account with which you have purchased music must be authorized separately. You can have multiple accounts authorized on the same computer, and can authorize each one using the Store, Authorize Computer menu item from within iTunes, or by simply trying to play the purchased content (which will normally prompt iTunes to request your authorization credentials if your computer is not already authorized).
Note as well that if you have audiobooks that were purchased from Audible.com, this requires a separate authorization process from your normal iTunes Store authorization.
You can determine which iTunes Store account was used to purchase a given track by selecting that track and choosing File, Get Info. The Summary tab will indicate the name of the iTunes Store account and date of purchase:
You can confirm that your computer is authorized for these tracks by attempting to play one of the tracks that will not transfer to your iPod. If the track requires authorization in order to play, you should be prompted to enter your authorization credentials. If the track does in fact play, this means that your computer is authorized for that particular iTunes Store account, and the track should transfer to your iPod without any problems.
Note as well that any given iPod can only support up to five (5) different iTunes Store accounts, so if you have loaded music from other computers that are authorized for different iTunes Store accounts, this may affect your ability to add music if you’ve reached this limit. Restoring the iPod normally resets this limit however.
If you’ve confirmed all of the above and your tracks are still not transferring to your iPod, you can try DEauthorizing and REauthorizing your computer via the iTunes Store menu. If this still does not help, you may want to contact iTunes Store Customer Service for more assistance.