AW 1st Generation Stuck on "You Need to Update to Pair"

[MacCubed]

This is a bit of a weird issue I am having with my first generation Apple Watch, I bought the device when it first came out, and used it for around a year until I knocked it into a door and cracked the screen. To replace the screen was $249, which was half the cost of the device, so I decided to just put it in a drawer and go back to a normal watch. Recently, I was curious to the price of replacement screens on eBay, and found them to be cheap so I decided to fix mine on my own. Upon powering it up, I found that the device was on watchOS 2, and since I didn't have the phone I used originally with the watch, I needed to reset it. After the reset, I tried to pair it with my iPhone on iOS 13, and the phone was telling me I needed to update the watch before it would pair. When I hit update it would try for a second, and then say that the watch was on the latest OS version, which it isn't. The watch would pair with an iPhone on iOS 9, but wouldn't update, and on iOS 10 it won't pair period. I called Apple support and they couldn't figure it out, so I thought I would ask here before I just bit the bullet and bought a new one.

 

[Lubidubi]

Had the same problem and apple set up a free repair to update the watch to the latest watchos. But in your case I think they wont do that, cause of the broken screen.