Lager1,
First, I'm unable to see an option under the File menu in Music to view the iCloud status of the songs in my library. I know I was able to see that when I first switched to iTunes Match, so I'll look harder.
One of the playlists that isn't syncing contains 4,405 songs on my computer and only syncs 79 of them. It's a smart playlist whose contents depend on a song's rating and whether or not the Description field has anything in it. I use that field to enter the date (e.g. 20230913) when the song hit #1 on the Billboard charts. After several unsuccessful attempts to create a similar smart playlist that synced correctly to my iPhone, I created a regular playlist and copied the contents of the smart list into it. That playlist synced correctly to my phone in a matter of minutes. So the problem I'm having may have something to do with the difference between smart and non-smart playlists, although that problem has only become apparent in the last two or three months.
Both my computer and my iPhone are updated to the latest releases. I'm considering bringing my entire Music library over to another MacBook to see if that has any effect in this problem, but I'm hesitant to do so because I'm not really sure how the second computer. For the moment I have my playlist that I can play in my car and that's a lot more than I had yesterday. But I also have 30-40 other playlists that aren't synching, so this problem hasn't gone away.
