Issues syncing music to Apple Watch

[wagszilla]

I cannot sync music (m4a files) to my Apple Watch anymore.

I've done everything here in attempts to troubleshoot the problem and nothing has worked. I've also tried disabling Bluetooth on my iPhone.

The watch waffles between the "Your music will resume downloading the next time your Apple watch is charging and connected to the internet" message and "downloading" but not moving past 1/8th done.

Anyone have these issues? How did you solve them?

 

[1rottenapple]

It’s wonkey ever since I got my Apple Watch 6 to 7 years ago. I have never had complete 100% syncing. I don’t think Apple wants us to load our purchased songs to the Apple Watch. They want Apple Music subscription.

 

[wagszilla]

My hope/guess is that it's related to me having iOS26 Beta on my iPhone since I haven't attempted to sync in months.

 

[wagszilla]

I think I've figured out the issue:

On Settings > Music there is a toggle for "Add Playlist Songs".

I can toggle this On (Green) and attempt to Add Music via iPhone (Watch > Music > Add Music) but this does not work.

After the attempt fails, the toggle for "Add Playlist Songs" is automatically turned off on my Apple Watch.

 

[1rottenapple]

Do you have problems with songs on the watch that’s supposed to be there and the watch not playing it. I get that a lot enough that I find it super frustrating.

 

[wagszilla]

The issues persist.

• For some reason the "Add Playlist Songs" toggle stays on now. No difference.
• I upgraded to Watch OS 26 beta. No difference
• I have no idea what happened but roughly 1/3 of my running playlist synced to the watch.
• All other playlists have not synced.

Do you have problems with songs on the watch that’s supposed to be there and the watch not playing it. I get that a lot enough that I find it super frustrating.

Yeah, it's done that a couple times. It'll load the song/cover art but it then skips to others.

 

[1rottenapple]

The issues persist.

• For some reason the "Add Playlist Songs" toggle stays on now. No difference.
• I upgraded to Watch OS 26 beta. No difference
• I have no idea what happened but roughly 1/3 of my running playlist synced to the watch.
• All other playlists have not synced.

Yeah, it's done that a couple times. It'll load the song/cover art but it then skips to others.

Yah same. This is my second Apple Watch the ultra gen 1 since 2021. I previously had series 5. I never resolved this issue which makes me believe Apple just doesn’t want us to use our music with the watch. Subscription service rule the day. When I get the notion to retry using my watch with my music which I did the other week at the gym I always run into an issue and give up.

 

[wagszilla]

When I get the notion to retry using my watch with my music which I did the other week at the gym I always run into an issue and give up.

Yep, my feelings exactly. I've tried everything. It's under 1-year warranty so I'm gonna try to complain and see if they do anything about it.

 

[wagszilla]

I scheduled an appointment at the Genius Bar for tomorrow. Maybe they'll help me or replace the watch.

Hopefully we can get it fixed.

 

[wagszilla]

Told me to wait until iOS26 is officially released.

Hard reset of both my phone and watch seem to be the next option.

Sigh.

 

[shapesinaframe]

It’s never worked for me with podcasts. Had to use a third party app and transfer over Bluetooth with my iPhone because the way wifi works on the Apple Watch is complete trash.

 

[wagszilla]

Still doesn't work after the official iOS26 release.

I really don't get it.

 

[wagszilla]

I had another appointment at the Apple Store.

The Geniuses didn't have any idea. I seemed to know more than they did. Solid guys though.

If anyone has a work around or has run into the same issues as me, please let me know.

🙏

 

[Markakett]

I’m having a similar issue but with MPEG-1,Layer 3 (MP3) files. I have a playlist for running consisting of 27 songs. Each song is approx 55 minutes long, the size ranges from 60MB to 150MB. These were previously downloaded to my Ultra with no issues. In a moment of stupidity I removed the playlist from my phone to allow more storage for photos on a recent trip. After returning and updating to iOS26 I was unable to add the playlist back to my watch. I have tried a few things, converting to AAC, or just adding 1 song instead of the whole list but no luck. Other playlists download with no issues so I’m sure it’s something to do with the size or format of these songs.