Music-Playlist is not synching to my iphone

I have several curated playlists that I use frequently on my computer, I synced my favorite playlists on my iPhone but there is one playlist that I have that I can no longer sync. No idea how to fix. All the other playlists sync fine except this one. I double checked the sync settings and this playlist appears in the sync settings but does not show up on my phone. I Have a Mac Pro computer with current up to date software and an iPhone 14 Pro Max also with current software. The issue is not recent, I've had it for several months so I don't believe it's a software issue. any ideas would be helpful. Thanks in advance.