So I seem to be having problems with Apple Music on my Apple Watch after upgrading to WatchOS 5. Basically, my music will not sync overnight to my Apple Watch when its plugged in. I plugged the watch in last night during bedtime and all the for you and heavy rotation playlists all have cloud icons in the corner. So when I tried listening to music on my Apple Watch without any internet connection, it initially played the first few songs then it stopped playing the next after that. What even happened? It used to download songs overnight when plugged in before the update.