Ive seen a lot of other people complain about this and honestly don't know why Apple has not fixed this yet. disconnecting the iphone from wifi and letting only the watch connect to wifi(no success).factory resetting the watch( will sync the same amount of songs then stop again).deleting and adding playlists (deleted playlists will not be able to be redownloaded).restarting both the iphone and watch and closing the apple watch app(no success).After the third playlist with plenty of storage left, it shows "waiting" and never progresses.
Ive had my apple watch 3 for a bit now and initially, it synced music slowly but still did it.
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