One of my computers will not play my Protected AAC audio files

Hi and thanks. I tried Safe Mode (didn't work), and reinstalled the OS (also didn't work). I went through the steps to create a guest account, but couldn't find a way to import the protected AAC files into that account. I have a sneaking suspicion that they still won't play, though.

I should mention that the AAC files in question play just fine on my MacBook Pro, which is on the same OS as this iMac (Catalina 10.15.7). They just won't play on this computer; sorry, I just noticed that I gave that info on the OP.

Any more suggestions, folks? I have 200 Protected AAC files on this iMac that just will not play. They each force a prompt for authorization when I try to play them, then when I enter the info, a new prompt appears saying that "this computer had been previously authorized, it has been re-authorized". But they still won't play. Like I said, the same files will play on my MacBook Pro.

Just an update to this discussion: the tracks that won't play on my iMac with MacOS Catalina also won't play on my iMac with MacOS Big Sur 11.5.1, and I've reloaded the OS to them without any success. As far as removing the files and re-downloading them, the iTunes Store does not show "Get" when displaying the songs I'm looking for; it simply lists their prices. I don't even know if Apple has a record of me buying the tracks (it was maybe 15 years ago). If there is one, I can't find it.

Still looking for some sort of solution to this.....?

Thanks.

Thanks, Jim. Didn't help, because the only thing that shows up in my "Purchased" in Music is a U2 album that was a free download a few years back. Nothing else. It's very strange. I've purchased several songs/albums over the years, and not one of them shows as being available to re-download (and yes, I've trashed/deleted the files that won't play).

Hi again Jim, and thanks for responding. I have no hidden purchases (I double-checked the Account window in Music).

I should say that I've also been on the phone and in chats with Apple Support during all this, and it seems no closer to resolution. The only hint of what *might* be happening is that most of these Protected AAC files that I own were purchased with an older Apple ID (that I no longer have or remember the PW to). However, all the song files do play fine on my MacBook Pro, iPhone and iPad, just not on my two iMacs (one iMac is a 2017 with OS 10.15.7 Catalina, same as the 2014 MBP that plays the files, and the other is a 2020 with OS 11.15.1 Big Sur).

Newest update: I recovered the Apple ID that the Protected files were purchased under (some 15-18 years ago), and now when I attempt to authorize the iTunes Store to play them, I get the following message: "There was a temporary problem completing your request. An unknown error occurred (5005)."

Needless to say, I've re-tried that attempt several times now, and always with the same result. Now what can I do?

Hi and thanks for your reply. As you can see in the OP, I did speak with Apple support.