My Mac will not synch music to iCloud

I have confirmed that my devices are all logged into the same Apple account (there's only me so no reason it would be another account). I have authorized my Mac. I have restarted the machine.

Nothing I try seems to get my music to synch to the cloud so I can hear it via other devices.

I have dozens of songs with "waiting" in the Cloud column in music.

I have gone to Library -> Update Cloud Library multiple times. I don't get the popup window either where you can see the progress.

Has anyone else found a fix for this?