Not authorized to play songs, with error message preventing authorization.

Hurrah! Your suggestion worked!!..

I was able to put all music that didn't play in a playlist. I drug them over to an external disk (a sd card, as I don't have a cd burner, and it's too many to upload to iCloud's limited data allowance). I then deleted all those songs from the iTunes play list -- told it to move those files to the trash. I then rebooted the computer. Then drug the songs back into iTunes. They still looked locked (padlock on icon). The first one I tried to play, I was asked for authorization. I tried to authorize it, and IT WORKED. No error message. IT PLAYED. All of the music plays, all 300, just by authorizing ONE of them. And, it retained the memory of how many plays, and most (not all) ratings. The only significant difference is that it says all 300 songs were added today, under the Date Added column. Small price to pay to have my music back.

And I still think Apple should fix it's useless error messages.

So I guess it's off to Apple Support. Thanks for your efforts.

I've done some more investigation on my problem, and I have new information. The "Not Authorized" is not on old CD's I imported. Sorry I mis-spoke earlier.

Instead, I can not play any song I BOUGHT from iTunes before December 31, 2008. Songs I bought in January 2009 up to now play fine (I think, I haven't tested them all).

This impacts over 300 of my songs. So, I could re-download them (as has been suggested on similar threads), but it will take me FOREVER to re-download that many songs. And why would every single song I bought in 2008 and before get corrupted? I would appreciate any help. Thank you.

Yes, I did change my email associated with my apple ID, late in 2006. So all my music that won't play, I get asked for the old email apple log when I try to play 2005 and 2006 songs. But when I try to play 2007 and 2008 songs, I'm asked for my correct apple ID.

But the result is the same -- two error messages that tell me an error occurred and to try again later. So, I don't think that is the basis of my problem. But thanks for trying to solve this.

And whatever, I do NOT have time to re-download over 300 songs. I shouldn't have to. I already paid for them.

Thank you. I’ll try your suggestion and let you know if it works. I think it will because the problem songs that I have on my phone, will play on my iPhone, just not on the computer.

and whatever, Apple should fix their error messages.

Well, your suggestion worked, for about a week. Now the songs again won't play. Why? Did I do an OS upgrade? Does this mean that every few weeks I will have to copy the songs to an external disk, and reload them, and then re-establish the rating and playlists? This is driving me NUTS. I just want to play the songs I bought -- hundreds of them.

So I tried apple support, and chose the email option. The nice person trying to help me kept directing me to iTunes for windows -- no, this happened after I upgraded my macintosh to Catalina. That's a macintosh, not windows. So then they told me click on the link for support. I tried it, and support won't answer. I filled in the form, and kept clicking on the "continue" button, and nothing happened. I tried over and over, for hours. No support is available. So I tried phone support. I know it will cost me money, but it has to be cheaper than re-purchasing all my songs. But phone doesn't work either. I've been on hold forever.

Another problem I had with this method is that iTunes lost all memory of what playlist I had put these 300 songs in, and it's a pain to replicate that.... but again, at least I can play my music.