I have been facing this issue since WatchOS 7.0.2 was released and I updated my phone to iOS 14. I followed many of the steps included below but not limited to: Hard reset of watch (Series 3 42mm aluminum non-cellular) Hard reset if phone (X) Deleting all data on watch Deleting watch app Resetting network settings Switching to a 2.4 GHz network What finally fixed it for me was taking the watch off the charger and putting it on my wrist. I believe before the update I had a message saying there was not enough space to download the update, but I cannot be sure. Deleting all data may or not be necessary, but try putting it on your wrist.