Apple Music Smart playlists not syncing purchased music

[Le Big Mac]

I have smart playlists set up - basic idea is songs I haven't listened to in x months with other limits.

When I sync from Music app to phone it shows in Music that it has sync'd all songs meeting criteria. But on iPhone not all songs show up in the playlist. Those songs are, however, "on" my phone in the general songs library.

The only pattern is that they're all purchased or protected AAC files, but there are also some of those that *are* sync'd correctly.

Overall it's syncing only about 60% of the playlist to the playlist on the phone.

Any ideas for a fix?

 

[Le Big Mac]

For anyone coming across this, I believe I've found the fix (though there seems to be a bug).

If the song is already synced to your phone via another playlist or, in this case, downloaded directly from Apple Music, then the sync engine will not sync the song in your smart playlist.

In my case I had to turn off "show all purchases" in Settings-->Music. Once I did that, the sync engine didn't "see" those songs on the phone so they synced as part of the smart playlist sync. (I also had to manually delete all those songs from my iPhone).

Now I'm seeing this also occurring with songs synced as part of a normal playlist - i.e., if the song is on a regular playlist (call it "my favorite songs") it won't also show up in the smart playlist that's synced.