The only conclusion we can draw from that is that you finally found the right combination of actions, in the right order, at the right location and with the moon in the correct position relative to you to allow the process to complete. There are so many variables within just a telephone and a watch to make troubleshooting stuff like this a complete wild goose chase. You could have had problems because of another Bluetooth enabled device nearby, or a conflict with another app on the phone that did get updated in the interim, or something else entirely. We all know the quote 'Insanity is doing the same thing over and over again, but expecting different results.', sadly, in computing, we have to do exactly that at times...