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I had a similar experience last week and spent over an hour with customer support. I was fortunate to get a rep who did not force me to try things I had already tried. After checking off a few boxes in her checklist she passed me on to her supervisor who eventually fixed the problem. The breakthrough seemed to occur when she asked me to forget the wifi network I was attached to on my iPhone and rejoin it again.

In thinking back through that experience I find myself wondering if my particular home network setup was contributing to the problem and possibly clashing with iOS 14's new private address feature. I turned that off when I updated my phone and watch awhile back but then forgot about it, and it seems that every restart of my phone (and/or watch) turned it back on, possibly impacting the whole update process.
 
Got a series 5 yesterday which I tried pairing with my 11 pro , it prompted to update 7.0.2 to continue pairing. The download starts , then when it’s about to finish, the unable to verify comes up. Please help. View attachment 977999View attachment 978000
After trying all possible solutions, I tried pairing with an iPhone running ios13, switched of the phone, then did the update directly from the watch connected to a WiFi , boom! It updated successfully! Then I unpaired and connected it to my phone. I guess it’s an issue with iOS14.
 
Tried all day yesterday to update my nike series 4 and it kept giving me the not connected to the internet BS. Decided to try my SS series 4 this morning and it is currently installing. going to try the nike again once the SS is done...
After trying all possible solutions, I tried pairing with an iPhone running ios13, switched of the phone, then did the update directly from the watch connected to a WiFi , boom! It updated successfully! Then I unpaired and connected it to my phone. I guess it’s an issue with iOS14.
 
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