How to simultaneously pair AND update Apple watch?

Ok, this is frustrating, but I am finding the process of pairing a reset and unpaired watch to be an endless loop. Why does an update need to happen before a successful pair? The update can't happen because the watch won't use the phone's internet. Heck, if an update is required, and the app clearly knows this, then the app SHOULD download the update for the watch. Instead the app serves the "unable to check for update" message?

I have a watch 2. Ever since I unpaired it and reset it for a repair at the Genius Bar I have been unable to pair the watch back to me. Whether I follow the automated or manual pair steps, the process always ends up with the "unable to check for update" message. Yes my phone is connected to the internet, both cellular and wifi. And the watch clearly knew the right moment to send a code for manual pair with my phone. That IS clearly a connection with demonstrated access to my phone's app and my phone's data. All the configuration and setup should continue through the app. I am even posting this message this very moment as evidence of an internet connection on the phone. Still, while the watch pairing process is entirely driven by the phone app, it appears that the watch ignores the phone's internet connection when looking for a software update. Surely it can update software later, but I digress. This seems more like an app problem than a watch problem to me. Anyways, I haven't found any solution yet. Manual Pair sounded the most promising solution, but the same "you are not connected to the internet" message (but I AM connected!) still occurs.

If this sounds like a familiar problem that you have resolved, I welcome your wisdom. I have found many older postings about this that seem to die off without resolution so I am posting now because I am still searching for that successful solution.