As Surface partner we are in close contact with the distributor and they told us to try the Suface connectors (USB-C>HDMI2) but that does not change a thing. I noticed that when this happens I need to power off the monitor and unplug the power cord of the dock. Wait for 20 seconds and reconnect everything. Then it starts working, but it is very enoying. Everything connected so everything is not available. Audio, cam, conferencing..
I'm out of ideas. I think we need a firmware update or more hardware to keep testing. I wonder what would happen with different monitors. Really disappointed with the Dock2. I won't be selling that until this is fixed.