Apple Watch SE 3: Music sync stuck on "Waiting
I got my Apple Watch SE 3 on Friday specifically so I could run without my iPhone 16 Pro in my pocket, and I want to physically download a mix of songs to my watch for workouts. I do not use Apple Music subscription service nor any other streaming service - I manage my audio on phone manually by syncing with stored music on my computer.
I have tons of playlists on Apple Music on my phone. Every time I add a playlist or album through the Watch app, however, the playlist shows up on my watch and album art syncs but there are spinning wheels next to the songs. It constantly has a "Waiting" flag that says the download will start "once your Apple Watch has a better internet connection." I have high-speed WiFi and the phone and watch are both attached to it.
Adding to the frustration, after multiple reboots/factory resets/toggling bluetooth/moving on and off the charger as suggested on social media, I was able to get one 400 song playlist to download successfully. The spinning wheels became solid gray circles and then one by one downloaded and displayed an arrow when finished. I can play that playlist without any issues away from my phone now.
But when I try to add another playlist (my primary running mix) I'm back to square one. And I've tried about a million toggles of every option possible short of another factory reset (because I don't want to lose the one playlist that did download, nor be forced to factory reset every time I want to add new music to the watch in the future). I am not near the 16GB media limit. Desperate for a solution as this was my whole purpose in buying the watch.