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I synced 255 songs in 25 min or so. It seems to go faster when you plug in the phone and leave both devices alone.
 
Got back home, restarted the sync, and in 5 minutes it was done. So all in all, about 10 minutes to sync. And all my songs were in the cloud, not on the phone. Impressed!
 
Now I'm having issues. I wiped both watch and phone over the weekend and set up each from scratch, no restore. That alleviated nearly all the bugs I was seeing. I was able to sync a playlist to the watch on Sunday but I wanted to sync a different playlist but it just says "Sync pending". Both watch and phone were charging and I did a hard reset on each two or three times.

It's not the end of the world because I already have some music on it but I'm just surprised nothing is working to force the sync, after a clean install.
 
I was, am still having issues making it work consistently. Sometimes my playlist syncs fast and I don't have any problems and other days it gets stuck. Eventually I get it to work but not when I need it to be done fast. I left a suggestion at :apple:.com for an update that lets us use iTunes and the charging cable or wifi to move the songs directly from a computer to the watch. That's the way iWork apps move files now and it works good enough. Certainly better than this current method.

I ngs I've tried to make the playlist sync:

adding and removing watch apps
opening and closing the apple watch app on the iPhone
opening activity app on iPhone and watch
adding and removing glances and complications
changing app layout
turning Airplane Mode on and off
toggling Do Not Disturb on and off on the watch

I've never seen any of them have a direct impact on the speed of the sync and most even stop or slow it down, lol.
It's broken somehow.
 
I found that to sync without any issues you need to have the watch plugged into the charger. Also, as has been mentioned I am only able to have one playlist synced at a time.
 

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This is the first I've read about any music syncing problems & im pretty bummed to read it.
The only reason I'm getting the watch is for fitness purposes & having music on it for the gym.
Though I won't be switching playlists a lot. I've had the same 300 songs on my shuffle for over a year.
Hopefully I get at least 1 good sync right off the bat & I'll be fine for a while.
 
This is the first I've read about any music syncing problems & im pretty bummed to read it.

The only reason I'm getting the watch is for fitness purposes & having music on it for the gym.

Though I won't be switching playlists a lot. I've had the same 300 songs on my shuffle for over a year.

Hopefully I get at least 1 good sync right off the bat & I'll be fine for a while.


Check your settings in the watch app is set to 2Gb, as its 1Gb default, I suspect your playlist might be just over 1Gb.

My music synced fine first time.
 
2 song playlist and just sitting there plugged to power...did the re-pair, and still no go.
And then my Mac told me low power on USB and to replug phone.
The moment I did, the sync started!

Super slow as well.

But then started over after 87%, and then stuck at 99%.

Toggle Bluetooth did the trick, complete sync and much faster.

Larger playlist sync today was good normal fast sync - both devices on power prior.
 
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Had to unpair Watch and iPhone to get out of sync pending purgatory

After much effort on my own, I finally called Apple Care. Guy was very good, and went right with doing an unpair of the iPhone and Apple Watch, and then a re-pair. It takes time at each step, maybe especially the music part, but all those electrons must be placed in the exact right position :).
 
I have a different problem. How do I unsync 600+ songs or almost 2.5+gb? I don't know how it happened it just happened. I open my music app to sync a playlist I created and suddenly all my songs are in there.
 
Not sure how you were able to do that, since the Apple Watch has a 2GB or 250 song limitation. Anyhoo, just go to the Apple Watch app, scroll down to Music, select Synced Playlist, and choose None.
 
I have 178 songs on my Apple watch. The syncing was straight forward. The only problem I had was that by default the limit was set to 1GB of songs, so only half of my songs were transferred to my watch. Once I changed the limit to 2 GB all of my songs were transferred to my watch.
 
Not sure how you were able to do that, since the Apple Watch has a 2GB or 250 song limitation. Anyhoo, just go to the Apple Watch app, scroll down to Music, select Synced Playlist, and choose None.


That has been checked since first day as I don't like music on my watch take over space. I reset it. Pair unpair. Then erase competent again. I only need like 50 power songs. Not 600+. Apple doesn't have a solution too.
 
I sync'd 2 GB worth of music, which I think was about 240 songs , but I found out one thing they don't tell you: BOTH the watch and the phone , no matter what the charge level , have to be on Chargers.

The sync took 6 hours.
 
A couple of weeks ago I synced a 540MB playlist overnight. Not sure how long it took since I was asleep. Then I upgraded to iOS 8.4 and iCloud Music. I made sure that the new playlist I wanted was all on my phone* and not in the cloud. The watch was on the charger as it won't even think about syncing otherwise. After 20 minutes of "Sync Pending" it began "Syncing." It reached 1% half an hour later.

I stopped it and created a 1 song playlist to test. The song was also on my phone. It took over an hour to sync a 5.4 MB song. My playlist is 143 songs. This is almost 6 days of leaving my phone and watch home syncing and not touching them. Obviously not going to happen.

I restarted both the phone and the watch. Same thing. I unpaired and paired them again. Still no good. It worked before the update to iOS 8.4. Now it doesn't work. Guess what I think happened? Yep, iOS 8.4 killed it.

*You can verify a song is on your phone by hitting the 3 dots in the circle. If it says "remove from device" then it's on your phone. If it says "make it available offline" then it is not.
 
Someone probably already said this but it goes much faster for me when I turn Bluetooth off on the phone. It will scream bloody murder repeatedly that I need to enable Bluetooth to communicate with the watch, but the music starts transferring much much faster. It seems as though you have to force it to choose wifi over Bluetooth for the transfer.

This is embarrassing for watchOS 1. That it's still a thing in watchOS 2...well....

ETA: some key details, I'm using an iPhone 5S. When I do the transfer to the watch, I make sure the phone connects to a separate 2 GHz wifi network I run specifically for my low-frequency devices. If your phone is connected to a single-band 5 GHz connection, I doubt the wifi transfer method works.
 
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For me it works. Watch starts syncing during battery charging. It is a little slow process becouse of Bluetooth connection. I had never enabled WiFi on iPhone to use Watch for remote controlling, calls, syncing etc. It works good.
 
I'm having a hard time getting music to sync to the watch. It says "Sync Pending", even when the Apple Watch is connected to a charger. It worked at first, but now it's being stubborn.

They should find a better way to handle this.

I found this thread while trying to search for a way to do this that didn't take all day. The watch, as it is, is practically useless outside of it being a neat watch, add to it that you have to wait 4 hours to sync a 185 song playlist via bluetooth (why not an iTunes sync option??) and I have to wonder what in the name of god they were thinking. Just not a very elegant way to use the thing, IMO. Its what it is I guess, and can only get better, but damn...I had to un-pair, re-pair and then wait a LONG time to get a simple playlist to sync.
 
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