could not connect to apple watch music synching

this was so very UNHELPFUL. the entire reason i bought the watch was for better accessibility to music without having to use my phone constantly. what is the point of having the watch if im going to have to redownload over 2,000 songs? please explain how to fix this better or just tell me that i’m going to manually have to import all my songs because then i can take the watch back because that’s actually so ridiculous.

I had a call with Apple support, who may have helped me solve this issue.

They suggested turning off WiFi on my phone, and then trying to sync. I did this, and as a side effect, my watch then prompted me to enter my Apple ID password. I had to type in my password on the little keyboard on the watch.

Since I did this, music and podcasts are synchronising just fine. I had to clear down the albums/playlists that were previously stuck, but I've just checked and my podcasts also synchronised overnight while the watch was on charge. Note: Music seems to sync when the watch is on battery, but podcasts require it to be charging.

So I would suggest trying the above, or another way to force iCloud to 're-authenticate' might be to do something iCloud related on the watch by going to Settings > Your Name > Password & Security and try changing your password, or manage a subscription or something (just a guess).

Apple support also had me sign out of iCloud and back in again on my phone, which didn't seem help. Mentioning it here in case it did in some way prompt that password prompt on the watch, but it didn't seem to be related (it only started working a few hours later when I disabled WiFi on my phone and tried re-syncing).

Hope this helps, let me know if you have any success.

Hello CDDB,

We noticed that you’re not using the latest update on your iPhone. Please use the steps here to update to the latest iOS version: Update your iPhone or iPad - Apple Support

" Update your iPhone or iPad wirelessly

1. Back up your device using iCloud or your computer.
2. Plug your device into power and connect to the internet with Wi-Fi.
3. Go to Settings > General, then tap Software Update.
4. If you see more than one software update option available, choose the one that you want to install.
5. Tap Install Now. If you see Download and Install instead, tap it to download the update, enter your passcode, then tap Install Now. If you don't know your passcode, learn what to do."

Once you’ve updated your iPhone to the latest version, we’d like you to test to see if everything is working as expected. If not, please contact Apple Support here: Contact - Official Apple Support

Let us know if you have further questions.

Take care.

Hello CDDB,

Thanks for using the Apple Support Communities!

If you haven't already, could you try restarting both of your devices and see if you notice any improvement after that?

Restart your iPhone

Restart your Apple Watch

Restarting can help resolve many common problems.

If that doesn't seem to do the trick, could you please confirm which OS version you're running on both the Apple Watch and iPhone? This will help narrow down what may be happening.

Cheers!

I had the same problem with my Watch 6 and a new iPhone SE 3rd gen. Both have the lasted OS updates. I restored my phone and couldn't get my watch to reconnect to it. I gave up and just reset the watch and restored it. Unfortunately since I don't have big iCloud storage, I had to restore my music to the iPhone via iTunes (which was OK since I need to "freshen up" my playlists). When next attempting to sync my music, I repeatedly got the same error message as the OP. Nothing found on the Google machine resolved it, and even a call to Apple support was no help. This morning I tried this:

1. Turned Bluetooth off on the watch.
2. Powered the watch off and back on.
3. Turned the watch Bluetooth back on.
4. Made sure they were connected - I "pinged" my phone thru the watch

I then attempted a music re-sync and it now appears to be working. I fact, it looks like all the music is transferring, and without me having individually select artists and/or playlists. (I do have Automatically Add Recent Music checked on.) This worked in my instance and I hope it helps others.

Marc

Any solution to this yet? I've recently started seeing this. Podcasts and Music refuse to synchronise until I restart my watch. After a 5 or so minutes, it starts happening again. I've un-paired and re-paired the watch, and it's not made any difference whatsoever. I am on the latest version of watchOS and iOS.

Using a Series 8 and iPhone 12 mini.

Hi,

I have exactly the same problem, with all the latest iOS and WatchOS updates installed, multiple reboots. Everything functions well… except the "Watch > Music" sync ( which fails with a “Could not connect to Apple Watch. Make sure your Apple Watch is nearby and not in aeroplane mode and try again” ).

The problem appeared approximately a week ago, circa 2023-02-10, and continues to this day.

Same here. Every time iPhone says „Could not connect to …“ Error. I don’t know what to do.

iPhone 14 Pro

Watch 6

Devices are all up to date with latest software. Also did multiple reboots, Airplane mode on off etc. nothing works here.

Nope, ManicMarc, no solutions. I do as you do — I restart my Apple Watch. That helps sometimes.

Also, keeping the total audio size under 500 Mb… despite having 25 Gb of free space available on the watch, as per General > About. 🤦🏻‍♂️

I'm having the same issue. I have a Series 7 watch, with the latest software and an iPhone XR with the latest software. I keep all my music downloaded on my phone, synced from my Mac. I would add or remove music historically from the Watch app (this is not my first iPhone or Apple Watch). The last six months it's been a patchy process. I'd add albums, but they'd disappear from the Watch app list, even though they were on the Watch. Now it's not allowing me to add music at all. Every time it either ignores me or I get the message "Could not connect to Apple Watch". All other apps works perfectly and the phone is very obviously connected. I have tried initialising and restarting many times, including a fresh install rather than from a back-up. Nothing seems to make a difference. I use Music on my watch every day at the gym and it's the second most important reason for owning one, so this is hugely frustrating.

Note: Certain albums can be added to the watch. Other get ignored or I get the connection message.

I was just having a download problem from my iphone to my series 6 watch after not having done such for quite a while.

shut down both, restarted and the problem resolved itself.

iphone started pushing selected music promptly to the watch when both were connected to power and wifi turned on - - -