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While setting up my new phone, the watch, which I was wearing, started trilling with the notification asking if I wanted to pair with new phone. I accepted and it paired up before my phone had prepared the 16.0.1 new update, which it had immediately picked up during the activation process. All very simple and easy, took essentially 30 minutes including Face ID set up. I chose to transfer data from old watch which seemed to be indicated as the faster process, and everything including apps was set up and ready to go in a short time.
 
My phone keeps popping up a notification saying “would you like to use this iPhone to set up Apple Watch?” Even though when I go to the Watch app it’s all paired and set up already. Restart didn’t fix.
 
Didn’t work for me, the phone kept saying it could not find the watch even though it saw it originally
 
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It did work for me. I’m still on series 5 watch but worked first time for a change.
 
It did work for me. I’m still on series 5 watch but worked first time for a change.
Did it bring the history from your old watch with it (settings, apps, health data, etc) and did you do this after everything on the phone was set up or did it prompt you before?
 
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Did it bring the history from your old watch with it (settings, apps, health data, etc) and did you do this after everything on the phone was set up or did it prompt you before?
I have a series 6 Watch on the public beta of Watch OS 9.1, and it asked once if I wanted to pair the Watch to the new iPhone 14 Pro in the middle of setup. I said yes, entered my Watch’s passcode, and the Watch restarted while I continued the phone to phone transfer setup.

When the transfer was done, everything on the 14 Pro was set up exactly like it had been on the 13 Pro, including the Watch stuff.

Absolutely seamless. Not that it was too bad before, but this was even better.
 
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I have a series 6 Watch on the public beta of Watch OS 9.1, and it asked once if I wanted to pair the Watch to the new iPhone 14 Pro in the middle of setup. I said yes, entered my Watch’s passcode, and the Watch restarted while I continued the phone to phone transfer setup.

When the transfer was done, everything on the 14 Pro was set up exactly like it had been on the 13 Pro, including the Watch stuff.

Absolutely seamless. Not that it was too bad before, but this was even better.
Sounds good. Did you unpair to force a backup for the watch on your old phone before starting or did it transfer and setup the watch without unpairing.
 
Sounds good. Did you unpair to force a backup for the watch on your old phone before starting or did it transfer and setup the watch without unpairing.
It sets up without unpairing. Even if you choose to set up with an iCloud backup it won’t need to unpair however depending upon when that iCloud backup was performed the very latest watch data may not be added. So the direct transfer would be the preferred method when the watch is involved.
 
It sets up without unpairing. Even if you choose to set up with an iCloud backup it won’t need to unpair however depending upon when that iCloud backup was performed the very latest watch data may not be added. So the direct transfer would be the preferred method when the watch is involved.
Interesting. Does the transfer unpair from your old iPhone or are you paired on both phones.
 
Interesting. Does the transfer unpair from your old iPhone or are you paired on both phones.
I did not check since I wiped my phone soon after the new one was set up, after I was confident everything had come over. But even though two watches can be paired to one phone I don’t think one watch can be paired to two phones. I’m assuming it was being unpaired at the same time. But I can’t say for certain.
 
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It was a pretty poor experience for my Series 3. That said, I fully understand it's a S3. I just reset the watch and paired it with my 14 Pro like new. I had a watch back-up available and I just restored that.
 
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Did it bring the history from your old watch with it (settings, apps, health data, etc) and did you do this after everything on the phone was set up or did it prompt you before?
All the history copied over. It gave me the prompt after the phone was set up.
 
Tried moving my Series 6 from my iPhone 13 to my iPhone 14 and it failed to work. I was on 15.7 with WatchOS 8 on the 13 side. When the 14 asked to move my watch over, I selected yes and it did not do anything. The iPhone completed and the watch was still on my iPhone 13. Nothing could get it moved over and I had to unpair then pair new. Lost my watch stuff. Unhappy with that.

Thinking back, perhaps I should have at the S6 on WatchOS 9 and the iPhone 13 on iOS 16 first. Not sure.
 
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I had 2 watches (S0 and S6) connected to my old iPhone 7 Plus. After transferring everything over to a new 14Pro, it automatically asked to pair my S6 to the new phone, and after that everything on the S6 watch was set up as before. In the All Watches menu in the Watch app on the new phone, both watches showed up but the old S0 was not paired. Pressing the pair button there would not pair the watch. Only after unpairing the S0 on the old iPhone could I successfully pair the 2nd watch to the new phone. I then also had to manually delete the original un-pairable S0 entry in All Watches.
 
I finally got my new phone delivered last night so was able to set it up. I used device to device to transfer but elected to unpair and do a backup to iCloud vs automatic transfer for the watch. Once the data transfer was complete I updated to IOS 16.0.1 and paired the watch manually. I restored using the backup from the unpair that was on the new phone. Everything seems to be ok.
 
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