The very first time you connect to a watch a data encryption key (RSA key) must be acknowledged that will very briefly show up when trying to connect to the watch. If you don’t press it fast enough it will disappear and not show up on subsequent attempts to connect.
Also go to your settings and make sure the wifi is on (sometime sit will show it is on, but it needs to be refreshed as routers sometimes drop connections, so try to refresh it
by toogling it off and then on (it happened to me just 2 days ago). Lastly get the ip address from the WiFi setting from your watch starting with192.1.168. the last number is very important and input that in GWD when the prompt shows up “of trying to connect”. some times it mat take 4 or 5 trys and most importantly stay very close to the router(the wifi bands on the watch are good but small so the range is limited and use the 2.4ghz band on your router).
You need to connect to get DUID for your device to generate the certificate. Once you have the certificate you can generate a .tpk and run on the device.