It is that darn RSA Encryption Key acknowledgement. Hold down the home key until it says rebooting it will take about 15 seconds or longer.Restart (not turn off and on) your computer to clear any caches there as well.

Next time you go to connect to your watch with GWS look very closely at your watch and an RSA Key acknowledgement will pop up. OK it. This does not last very long and if you do not acknowledge it the watch will see it as an attempt to hack your device and set it to NO and not show again.

That should be all the problem since you were able to access the device to create the distributor certificate it is just that one thing blocking it.

By the way you might want to turn the developer options on by tapping on the software version 5 times in the about watch settings. If you accidentally have OPR too high for the AOD it will allow it to load.

RonSamsung Developer Program

That is the reason why Samsung is failing. The problem was reported at least 1.5 years ago but the customers are still forced to struggle for hours & days with the same issue.

Again & again & again.

Try again to reboot the computer and watch… Wait a full minute before connecting after they reboot.

FWIW this is necessary to comply with new Privacy laws in Europe, USA and elsewhwere