I am also having this issue (Apple watch 3 and iPhone 11.) I only subscribe to Pandora to be able to use my watch without phone to play music when I run. I also get the message that the watch will sync downloads when near the phone, but this never happens. I guess it’s time to bite the bullet and pay iTunes (or now Spotify) for a solution that actually works. Also, trying to access and play downloaded songs on my phone via Car Play (in my VW) is a major hassle. These are major technical issues that need to be resolved, or you will continue to lose subscribers… (obv)
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