Some songs won't sync to my Apple Watch

I was having a similar problem (just bought a watch series 3 yesterday) but then realised the issue might have to do with the "automatically add" section ..

So as a workaround --

If you add playlists manually using the "+ Add Music" function (disable anything in the Automatically Add section), you will find they will all be uploaded to your watch (provided its charging). An Updating Bar appears on the top of the screen - it can take a while so you need to be patient lol.

Remove a playlist from Apple Watch

1. Open the Apple Watch app on your iPhone, then tap the My Watch tab.
2. Tap Music > Synced Music > None.
3. To remove the playlist, set your Apple Watch on its charger and make sure it's charging.

From: Listen to music on your Apple Watch​

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I'm having the same issue. In general, syncing music to the Apple Watch has been a painful, buggy experience. Initially, it wouldn't sync at all or it would sync up to 98% and appear to stop. I've done all the steps that have been suggested (numerous times), including switching to new playlists, rebooting both the watch and my iphone, installing the latest software updates, as well as un-pairing and re-pairing the watch to the iphone (note to anyone who hasn't tried this: takes forever, do at your last resort).

I am finally able to get the watch to sync. But it inexplicably leaves out random songs. The app says they've all been synced, but when I look on the watch, some tracks appear greyed out and cannot be played from the watch. I've compared all the tracks to see if I can figure out why some songs won't sync, and I cannot find any discrepancies... I tend to buy all my music from Amazon, so they're all the same file type and bit rate.

This is extremely frustrating. Syncing music to the Apple Watch is not up to Apple's typical standards... I don't understand why the watch doesn't appear in iTunes when connected like an iPhone or iPod and we can't simply drag/drop files.

Yup same here. Normally I have my fon with me at all times but recently my emploryer decided we arent no longer to have our fons while working so i figured id just load em to my watch and play em thru my Bluetooth head set........ 3hrs later im beyond frustrated. i expect things not to work with windows or android and even a little glitchy perhaps using ubuntu but apple? their in a league all their own when it comes to having things just plain work.

Same for me! Just bought this watch yesterday specifically for listening to music without a phone. Can’t believe this isn’t working!

Thank you Jonathan. Yes both my iWatch and iPhone have the latest updates.

I am experiencing the same problem. I've tried all kinds of different things and no matter what, this one particular song will not sync to the watch. Every other song in the playlist will sync except for this one specific. Idk what to do. :/

I've been having this issue for months, and no updates have ever fixed it. I even pay for Apple Music, so you'd think things would all sync up properly. I've tried restarting and completely resetting my phone and watch- no difference. 257 of my 290 songs (all less than 2.0 gb) sync, the other 33 songs refuse to sync.

I've had an Apple Watch since the very first one was released, and I'm now using the Series 2. There have always been weird issues similar to this. If WatchOS 4 and iOS 11 don't fix this, I'm just at a loss

Same exact experience from me. I moved over from Spotify to Apple Music assuming I would be able to create playlists under Apple's umbrella, assuming it would work correctly. So far, out of 145 song, it's synching ~10-15. Really frustrating. Like many others, the watch and app are both showing all the songs are there but they're not playing when I'm away from my phone. I've pulled the playlist off and added back on. . . power cycled and restarted both devices ad nauseum. What is the point of offering this as a feature if it's so buggy? It's an MP3 player, I'm not sure I understand why it's so difficult to get such old tech to work on the Apple Watch S2.

not helpful, have numerous attempts still not syncing full playlist seems to randomly decide what songs to sync and never the complete list of ~54 songs.

I'm also having the same problem. If the playlist has different artists the entire playlist doesn't download, only random songs on the playlist. I have tried syncing the playlist with only 1 artist and all songs sync correctly.

Hi

It may help to first play each affected track from the playlist on your iPhone (a few seconds for each track may suffice, rather than playing them in full).

Thank you but playing part of each song I your iPhone doesn't make a difference.

If you have not yet done so, it may help to update your iPhone and Apple Watch to the latest software, starting with your iPhone:

• Update the iOS software on your iPhone, iPad, or iPod touch - Apple Support
• Update the software on your Apple Watch - Apple Support

iOS 10.1 fixed some issues that may have prevented Music playlists from syncing to Apple Watch.

I am having the exact same issue. Thanks for posting. Is apple doing anything about this?