Apple Watch music sync from personal playlist stuck on watchOS 26

I am having the exact same problem. I have an AWU 2 and iPhone 16 Pro Max. I keep about 10 GB of music on my watch that are local files. No AM subscription. I unpaired my watch because the battery life was awful and repaired it as a backup. Then I could not transfer music. I have tried:

• unpair, repair
• unpair, re-pair as new watch
• updated software on both devices
• constant power cycling
• reset network settings on iPhone
• turned off cellular (only WiFi and bluetooth on phone) - no help
• put only WiFi on
• tried smaller playlists with only one song - I did get one song to transfer, but no others
• the transfer seems to reset as soon as my phone locks
• even if I keep the phone open, unlocked, the transfers never happen

This is so frustrating! There must be a bug - usually I'd just assign the playlists to sync and then it would do it while I was going about my day because you could request that it do it off the charger. Now I can't even do it on the charger.

Why have a $900 watch with 64GB of memory if I can't put music on it?!

Same thing happening here.

AWU2 with 17 pro max.

have unpaired and paired many times, erased and set up as new Apple Watch. Still cannot add any music.

Watch app says it will continue next time Watch is charging and connected to internet; which it has been the entire time

I bought the Iphone 17 pro max and the hermes watch Ultra 3 and althou all the rest of the funcation works , the main function did not wark was the syncing of my personal music. Even apple support was unable to help.

I just returned and moved to samsung no issue syncing to there watch ultra.