Samsung hasn’t allowed Bluetooth debugging on Watches for over 3 years and I believe that Wear OS will not allow it in the last or next update. It is considered a security issue.
For anyone else with the issue Here is my FAQ Answer. And command line connection seems to be the final solution when all else fails.
Your watch and computer need to be connected to the same WiFi network. Unplug or turn off the Ethernet adaptor if you have your computer connected by Ethernet
You cannot have Firewalls or VPN enabled.
Go to Settings
scroll down to About Watch tap on it
Scroll down to Software Info tap on it
Scroll down to Software Version tap on it 7 times and a dialog will open saying developer options enabled
Go to Settings
Allow the permissions as the watch requests them.
scroll down to Developer Options tap on it
Select ADB debugging tap on it
in those options, enable ADB debugging, and select debug over WiFi
it may take time to connect it took me about a minute before it shows the connection.
The first line will have your IP address followed by :5555 the :5555 is the port for debugging
Go to Connections and write down the IP address your router assigns to your watch.
From Watch Face Studio build your project with the wrench tool
Run on Device with the watch icon next to the wrench
It will search for your watch if it doesn’t find it. (it usually doesn’t)
add your IP address when you run on device in the + dialog and do the search again.
You Watch will pop up an permission to allow debugging or something like that select don’t ask again on this device allow.
After the restart run on device should work it will spin quite a while then say launch completed.
If it doesn’t
Using File manager copy the address where you installed adb by default
(copy the address as text from file manger using right click on the address bar)
Open a command prompt
navigate to the folder address
adb connect 192.168.x.x:5555 (where 192.168.x.x is your watch’s IP address).
It may take a minute to connect or give a failure response
If you get a rejected error or something check your watch debugger settings.
Try in developer options to revoked permissions and force new acceptance. do the connect again.
select “run on device” within Watch Face Studio, your watch should show up.
If it connects but will not run on device create a new keystore in a new keystore folder
p.s. I like your watch face it is unique and really a watch FACE
Samsung Developer Relations