iPod iPod won't sync even though authorized

[steve333]

I keep getting this message:
This computer is no longer authorized to play purchased items that are on the iPod “Steven Golden’s iPod”. Would you like to authorize this computer for items purchased from the iTunes Store?

Even after I entered the correct password and got the message that the computer was authorized I click sync and get the above message and again and again

 

[moozeekfan]

I keep getting this message:
This computer is no longer authorized to play purchased items that are on the iPod “Steven Golden’s iPod”. Would you like to authorize this computer for items purchased from the iTunes Store?

Even after I entered the correct password and got the message that the computer was authorized I click sync and get the above message and again and again

I know this is a late answer, but I was having the same problem with my Mac after I synced my iPhone. Did you change your Apple ID at some point (even if it was a couple years ago)? I had changed the email address I used at one point and when I went to sync my phone (which I hadn't done to a computer in the same amount of time), I got that exact warning and I was not able to access any of my music in iTunes Match also. Fun times.

Good news: You can eventually get this to work.
Bad news: It will take you 90 days (or whatever the amount of time is left to switch between Apple User IDs), I called Apple about this same issue and I was told there's nothing that can be done to speed up the time left or to switch the Apple ID to the newer account. It's been 90 or so days since you sent this email so maybe try again and see if it works.

 

[steve333]

I know this is a late answer, but I was having the same problem with my Mac after I synced my iPhone. Did you change your Apple ID at some point (even if it was a couple years ago)? I had changed the email address I used at one point and when I went to sync my phone (which I hadn't done to a computer in the same amount of time), I got that exact warning and I was not able to access any of my music in iTunes Match also. Fun times.

Good news: You can eventually get this to work.
Bad news: It will take you 90 days (or whatever the amount of time is left to switch between Apple User IDs), I called Apple about this same issue and I was told there's nothing that can be done to speed up the time left or to switch the Apple ID to the newer account. It's been 90 or so days since you sent this email so maybe try again and see if it works.

Apple said I had bought some songs using another email address (my mothers) but I would never do that. It's pretty screwed up that they can't fix it on their end. If all the songs are on one computer they should all sync at the same time regardless. Apple aint what it used to be