This worked for me too! Spent hours today and tried everything listed in here and other forums and kept getting the stupid error message when trying to update that I wasn’t connected to the internet, which I definitely was! Once I turned on Low Power mode, bam! Started updating! WTF?!

Try Low Power mode! I tried everything on this site and combined them even, this is what eventually worked for me

I have a series 3 watch and after spending hours trying to update the darn thing, read that someone suggested turning phone to Low Power mode, and voila! Now it’s working fine, new update and all!

I literally tried EVERYTHING listed in this forum (and others) spent hours trying to figure this crap out! What finally worked for me was setting my phone to Low Battery mode! Crazy