This issue is still happening. I have an iPhone X running on latest beta release and it's been a while I used my Apple Watch 4 series. When tried to pair the watch, I was not able to proceed further to pair as I see "Unable to Check for Update" error screen with Start over and try again options.
Do we have a tracking ticket for this bug?
Vinayteja
Users receive reputation points by contributing quality content to the forums.
Posts include post and replies published on the forums.
Post authors can mark replies as Accepted to indicate successful solutions.
Apple Developer Forums admins can mark replies as Apple Recommended to indicate an approved solution