Music (iTunes post Catalina) playlist bugs.. tracks not being added, nor synching to iPhone

[drmeatball]

I don't know if this happened back when Music was still iTunes, but I'm having repeatable issues with Music on Catalina not syncing playlists properly.

I drag a file from the Finder to the playlist in Music, it shows the file added to the list, but it really isn't. It doesn't sync to iphone, it doesn't actually play when I double click on the line entry, and it's never actually copied to the Library (I have the Copy Music Media option turned on - I check the actual folder that stores the library files). For all intents and purposes, Music claims that it has done what it is supposed to, but it hasn't. If I quit Music and redrag the file in a second time it works.

Every second time it works. Never the first. Extremely annoying. Anyone else experience this?

 

[Stephen.R]

I’ve noticed weird stuff with dragging files to playlists too.

If I have a playlist selected I can’t drag to it either in the main list or the Playlist name in the sidebar; I have to select some other playlist then drag to the name of the playlist I want to add to in the sidebar.

I think I’ve also seen dragged files get added to the library, but disappear almost instantly from the playlist I dragged them to.