I’ve been trying to figure it out, and I just got it to work recently. First, make sure everything is updated to is latest update. Then, make sure Iphone Detetion in the Apple Watch passcode settings on your phone is turned off. Then, try restarting the watch, your phone, and your computer. Then try it out. If it still doesn’t work, unpair and repair your Apple Watch and try again. If that doesn’t work, put your phone to airplane mode, and make sure your watch isn’t on airplane mode. Then try. Also try turning handoff on and off on your Mac and phone. If it still doesn’t work, please let me know.