Why does iTunes refuse to play MY songs that were uploaded from CD long ago?

Update: It appears the issue is with songs purchased on the iPhone will play on the iPhone but not the iMac or MacBook. I am not going to pay $11 a month plus tax to sync automatically the one or two times I buy a song on the phone. I tried syncing by connection but it won't because it says I don't have enough space on the iMac (mind you it's new and has 638 GB open and it says it's only 2.57 short and the phone only has 68 on it). It won't let me sync just music and keeps telling me it can't sync something that I don't know what it's talking about. This is sooooo frustrating. It used to be so easy. Literally plug and play and now it's as bad as any PC out there.

Yes. I imported the music into iTunes so it wouldn’t mess up anything already there. No I did not subscribe to anything. As I stated in my first post. Not going to pay for a service to listen to music I already own.

I do know that iTunes won’t work for libraries not stored on the Mac, but since yours is -

1. make sure the Mac is authorized.
2. Make sure you signed in to iTunes/Apple Music with the UserID you purchased the music with. If you have multiple user IDs, you will need to authorize each one. This turned out to be my issue. Apparently the songs that weren’t playing were purchased early on when I had iTunes on a pc before buying my iMac and getting a .mac user id. So long ago, I didn’t remember.

I copied the library to the cloud so I could add it that way since I wasn’t doing the normal transfer everything. I keep getting that idiot box telling me to authorize the computer to play the music. The computer is authorized. It still won’t play the music. My id and password did not change.

That didn’t work for me, but it was a good try.

However, the update his morning and the resulting restart may have fixed some of it. Suddenly music that was erroring is now playing. Still some that won’t and thinking those may be songs or albums I purchased and downloaded from Amazon because that was the only place they were available or I had credits to use. Going to go to my Amazon Digital purchases and check just those out before clicking on everything one by one to see if it works.

Update: started going through songs and it is a combo of songs/albums I bought and the free ones that iTunes gave away but not all of them. Go figure. Ended up contacting support. Chat bumped me up to higher tech chat who bumped me up to a call and they had to submit to the engineers because I shouldn't be getting the authorize computer message for music I own. I had provided a screen print of the iTunes Store showing my only option was to play a song (not purchase it) with the pop up that I'm not authorized. I mentioned that I'm not the only one having this issue as I have seen plenty of posts on the topic.

Do you have an iPod? It’s a good backup. Also, what others have said, if you have it in the right place on your new mac, they should play. Or if you put that folder on the new desktop - you should be able to import them into the new iTunes.

Also, make sure your have it stored in the correct place on your Mac.