Q: One song in iTunes won't play

Hello vickifrombenicia,

Thanks for using the Apple Support Communities. This symptom usually occurs when a song was accidentally purchased from a duplicate or separate Apple ID. Let’s check to make sure that you are authorizing with the correct account name (for this specific song), even if you feel very confident that you are. For more information, see this resource:

iTunes repeatedly prompts to authorize computer to play iTunes Store purchases - Apple Support

http://support.apple.com/en-us/HT203160

Authorize using the correct account name

The items you're trying to play might have been purchased using a different iTunes Store account. To determine which account was used to purchase an item, follow these steps:

 

1. Select a purchased song in your library and choose File > Get Info.
2. Click the Summary tab. Note the Account Name that appears in the list. This is the account name (Apple ID) you'll need to use when authorizing your computer to play this purchase.

 

Note: The account name that appears is the one you used when purchasing the item and does not change if the account name (Apple ID) changes.

 

If you've authorized the Apple ID that is shown in the Summary tab, you can check the purchase history for that Apple ID from Store > View My Account. If your purchase history does not reflect the purchase of the items in your iTunes library, consider any other Apple ID you may have created, and authorize the computer for your additional Apple ID.

If you’ve followed the steps above and the issue persists, you can try the additional steps outlined in the article.

Cheers,

Matt M.