Moto 360 Debugging Connection Issues

I can't seem to get my Moto 360 to prompt for authorization through to ADB with Bluetooth debugging. I've tried multiple ports, I've tried resetting the watch, and I've made sure (multiple times) that Bluetooth debugging is turned on at both the phone and watch (phone is USB to PC). ADB debugging is working just fine for the phone and the phone is already authorized. The Moto 360 never asks for authorization either on the phone or watch. Does anyone have any idea what the issue might be?

The particular error is 10061, cannot connect to localhost:4444 no connection could be made because the target machine actively refused it.