For anyone still having issues with updating their watch, I combined a few solutions I got from this forum and it worked for me and thought I might share. I was about ready to throw my watch away until I finally figured it out. First, I turned off cellular data and just kept my wifi on. Then, I made sure to hard reset my apple watch (hold down crown and power button then once you see apple logo, hold just the power button for 30 sec until you see red bar to erase all settings, then press that.) Then, I just deleted the watch app and redownloaded it. Just for a fresh start lol. Then, I attempted to pair my watch to my phone, but prior to actually pairing, I changed the language to Portuguese and location to Canada by pressing the “i” icon on the watch in lower right corner. Then, I finally paired and it actually worked. I pressed “update now” and it began to update. Not sure why this has to be so difficult to figure out. But there is a way, don’t give up! Fix it Apple!