For this year’s move of my Apple Watch series 9 to a new iPhone, the move required exactly zero effort on my part. This is so nice!
Previously, I recall going through various gyrations — sometimes having to unpair from the old phone and then pair with the new. So having it all happen automagically was a dream. Note that I had already upgraded my old iPhone to iOS 26, and my watch to watchOS 26, before activating and moving to the new phone.
That was my experience in the past… but not this year!
I kept getting error messages that my new phone couldn’t pair to the watch. I must have tried it 100 times. Nothing worked. I finally had to unpair the watch from the old phone and repair on the new phone. That worked, but it lost a few settings (some of my complications) and some of my settings (such as list view of apps which switched to icon view). Rather annoying.
I had no problem moving it at all, but the setting in Watch > Passcode > Unlock with iPhone was turned off in the process, which confused me for a bit.