Hi Mark de Medici,
Thank you for reaching out Microsoft Community. We're sorry for the inconvenience this may have caused you?
I have few questions below to clarify the current issue you're now experiencing.
At the back of your monitors, what are the available ports? Can you directly connect the USB-C cable from the Surface device or from the Surface Dock 2 going to the monitor? Or do you need to use an adapter for that? If the monitors has a USB-C port at the back of it, have you checked the monitor's technical specs if that's an input/output port? Just like any other devices and based on technical specs, the ports available at the back of the monitor have it's specification whether it's only an input port or an output port. So, this needs to be checked.
Relying to this link>>https://support.microsoft.com/en-us/help/4023496/surface-troubleshoot-connecting-to-a-second-screen, you will see that the port that allows you to extend the Surface display (based on device model) to external monitor without the use of the dock is being labeled as external display/audio output port. So, the ports at the back of your monitor has its own specification, too whether or not it can do both (input/output), like HDMI-in and out available at the back of some monitors and this is what I think could be the point of failure as to why it won't show any picture even if it's being recognized. Is it showing no signal? Or it's just completely black?
Please respond to this post as soon as possible so we can further check as to why it's giving you no picture even though everything is up to date.
Kind Regards,
Crest