Visual Studio failed deploy to HoloLens: Error DEP6957 : Failed to connect to device
I restarted the headset, I restarted Visual Studio and even the computer and was still facing the issues.
Eventually I determined that I needed to leave the headset pin window open while pairing and if you enter a bad pin into VS, it is hard to get/find the dialogue to change it.
As a result, I created a new build configuration which triggered the pin window immediately upon build, at which point I opened the pin/pairing dialogue in the headset and entered the pin while leaving the pin dialogue in the headset open until it showed the device as paired.