iTunes - stuck in authorization loop

Question

I just got a new laptop with Windows 7 and thought that instead of trying to recover my music from my iPhone, I would just use the Homegroup I have set up to transfer the music from my old laptop. Well, I did that, but now iTunes has decided that all of my apps, but only 3 of my songs (out of the 70-80 that I've purchased) cannot be transferred to my iPhone (even though they're already there) because I'm not authorized.

It will prompt me to log in and authorize the computer (which I had already done).

Once I log in, it will just tell me I've already authorized this computer.

Then if I go and try to play the song, it will just prompt me to authorize it again.

I've searched Google and tried pretty much everything I could find. I've tried:

1. deauthorizing -> logging out -> logging in -> reauthorizing
2. Reinstalling iTunes
3. Deleting the SC Info file

I've got 15 GB's worth of music, which doesn't transfer swiftly. So before doing anything drastic with my music collection, I thought I'd ask around here and see if anyone else had had similar issues, and hopefully found a fix.

Answer 1

You might have purchased some songs with a different iTunes account which will then not authorize, because the login details for that account, and its songs would be incorrect.

Answer 2

See this Apple Support article:
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases

It offers the following solutions:

• Authorize your purchases from an administrator account
• Authorize using the correct account name
• Turn Off User Account Controls (Windows Vista and Windows 7 Only)
• Remove the SC Info folder

If none of it helps, run iTunes by right clicking on the iTunes.exe program file from C:\Program Files\iTunes and selecting the "Run as administrator" option. Then select the Store | Authorize this Computer option from within iTunes. You will still get back the familiar message saying that the computer was already authorized, but this time it might be true.

You can try upgrading to the very latest iTunes version, the problem might have already been fixed.

You can also email Apple Support and ask for a list of accounts registered to your address. The account shown on the songs info might not be the account that can authorize them. It's also possible that something has gone wrong with your account, that an Apple engineer can fix, and especially if some old accounts of yours are messing you up.

Lastly, might it be that you may have already authorized five computers on your account? If that is the case, then you can "deauthorize all computers associated with your account" and then re-authorize yours by following the steps described in About iTunes Store authorization and deauthorization. As you remarked above, this is somewhat risky.

Answer 3

Worst case scenario, delete those 3 songs and re-download your purchases.