Hi All,
I have encountered all the of the same issues in this thread.....
4 days of pulling my hair out trying to find a solution to have the Surface Dock2 to display on dual monitors has been frustrating to say the least.
The solution that has worked (finally !!!!) for me, is that you need to purchase the Microsoft Surface USB-C to HDMI adaptor.
There was a post in this thread below about using an active USB-C adaptor, which was my final attempt to get this to work OR return all these Microsoft products back to the retailer for a refund.
Most retailers will only have Passive USB-C adaptors, which don't seem to work with the Surface Doc2. (I had tried multiple different adaptors - all were passive)
I highly recommend that if you are having this issue, to try the active USB-C adaptor method first, the cost of $64 per adaptor is small in comparison to the lost productivity time trying to get the monitors to work.
Hope this helps anyone having this issue.
Hardware Set-up :
Surface Pro 7
Surface Pro 2 Dock
Microsoft USB-C to HDMI adaptor
Generic VGA to HDMI Connectors
Dell 24" Monitor
HP 24" Monitor