Hey guys so I was having the same issue as everyone else but on an apple watch series 4. I went ahead and attempted EVERYTHING! Hard reset watch,Hard reset Iphone, reset network settings on iphone. I even signed out of icloud at one point. So the one that finally did it I think I reset watch then iphone and attempted to pair. It gave me the same message as always "Unable to Check for Update - Not connected to the internet error" but this time I just hit the try again like 15 times back toi back to back! no lie it seemed like everytime it looked longer for the update until it freaking worked! updated to watchOS8.0.1 I hope this was not a fluke and helps some ppl. REMEMBER hit the "Try again" button back to back to back mine worked like on the 15th time.

Hey guys so I was having the same issue as everyone else but on an apple watch series 4. I went ahead and attempted EVERYTHING! Hard reset watch,Hard reset Iphone, reset network settings on iphone. I even signed out of icloud at one point. So the one that finally did it I think I reset watch then iphone and attempted to pair. It gave me the same message as always "Unable to Check for Update - Not connected to the internet error" but this time I just hit the try again like 15 times back toi back to back! no lie it seemed like everytime it looked longer for the update until it freaking worked! updated to watchOS8.0.1 I hope this was not a fluke and helps some ppl. REMEMBER hit the "Try again" button back to back to back mine worked like on the 15th time.