The downer of having to do it at all is pretty annoying. Apple stuff is just supposed to work.
Sure is! There are two good watch apps for Tesla. Both have the same problem. I sent in a trouble ticket to
Watchla and
Watch for Tesla they got back to me with an explanation.
Seems that Apple increased it's security requirements for non-Apple watch apps like these two that I have tested that were designed by small entrepreneurs. So, while the virtual key to connect to my Tesla data used to be once and done, the key expires randomly now. To make it easy both apps added a button in the iphone to refresh the key. So when something like my battery state of charge is no longer responding, the fix is to dig out the iphone and open the app and hit the refresh button for a new Key. Then it takes about 5 seconds to update. If the Tesla is "asleep" to conserve battery drain it can take up to a minute before the car transmits the date to the phone and then it updates the watch via Blue Tooth.
I'm hoping one day Tesla will make an official app for the watch that refreshes automatically. They would have the clout to get approved by Apple.
Anyway, it is what it is.