So, I had this problem around the January update for my SP7 i7/256 hooked up to two different Dell monitors (2414H and 2415) through the Surface Dock. The funny thing is one monitor (2415) worked, but the other (2414H) was stuck on 640x480 resolution. But I took Barbara(?)'s advice from earlier this thread and rolled back my driver for the Intel Iris Plus Graphics to the older one, and both monitor went back to working fine. I know this error did not come from the dock because I was running this same monitor setup with my old SP3 and had no trouble whatsoever.
Recently, seeing how Intel was offering driver update to their Iris Plus Graphics outside of Windows Update, I decided to try an update and see if things work out. I installed the 27.20.100.8190 version, restarted SP7, but the 2414H monitor was now stuck on 640x480 resolution. Kind of disappointed, I was ready to roll back but decided to try another advice offered somewhere in this thread. I enable Displayport 1.2 on my 2414H monitor, and everything worked. (Well I did have to change my frequency from 59Hz back to 60Hz, changed originally to 59Hz due to another advice in this thread, to eliminate flickering.) But now both monitor works at their native resolution connected to the dock with the most updated driver.
I have tried most of the basic advice (reset SP7, reset dock, update stuff) when I first encountered this problem, but none of them worked for me so I rolled back the driver. But changing the Displayport version on my monitor made it all work.