Smart playlists played on iPhone not updated in MacOS music app
I manage music on my iPhone by creating smart playlist in the music app (formerly known as iTunes). The playlists are populated by least recently played, so when I play a song it falls out and a new one is added in. In the past, when I played music on my phone, the playlists would update both phone and iTunes when I synced my phone. Now, songs played on my phone are not updating the playlists in the Music app.
I just updated to Catalina, but the problem had started before the update.
iPhone 11 Pro running iOS 13.4.1
iMac (Retina 4K, 21.5-inch, 2017) running macOS Catalina 10.15.4 (19E287)