iMac not authorized to play song, won't copy to iPhone

Hi Steve Scherf1,

Thank you for using Apple Support Communities. We understand that you seeing an alert about authorizing your Mac to play and sync songs and we'd like to help.

Since it appears that you have authorized your Mac correctly, are able to initially play the songs, but then see the message again, we suggest you reach out to Apple Support directly here: Get Support

Cheers!

I've had the exact same problem, Steve, and I thought I was alone. Did some troubleshooting on my own and was eventually able to determine that the problem pertained specifically to Protected AAC files I had purchased from the iTunes Store between 2003-2009. I spent hours on the phone with Apple Support on the telephone explaining the situation. I was transferred this way and that, because no one had ever heard of the problem—I suspect they simply stopped providing support for Protected AAC files. Needless to say, they were ultimately no help whatsoever.

Here's what finally worked: I deleted the files (around 900 of them) from within Music, but opted not to "hide" them. Then I just re-downloaded fresh copies. I lost a few, of course, because iTunes no longer carries some of the particular tracks or albums I had originally purchased. Cost me $20-30 to replace them, but it seems to have gotten rid of the problem.

Do make sure, of course, that you delete them all from your iPhone 11 before re-syncing. You'll want to do that through Settings > General > iPhone Storage, and not through the Music app itself because the latter often simply leaves the files in place on your phone.

Hope this helps!

Butter

Interesting. If I encounter the problem again, I'll try that. What I think it comes down to is that Apple has simply stopped providing any support for the old Protected AAC files—the don't seem to incorporate them into software upgrades and updates. I suspect it's going to get harder and harder to use these files in the future. I wish Apple would just offer to replace them with the Purchased files, but that ain't gonna happen, now is it?!

Butter