Surface Pro 4 does not recognize my external monitors
This is a common symptom since Windows 10 CU. Two workarounds that I use are pressing Win+Ctrl+Shift+B or using the Project dialog (Win+P) to make a change in the display configuration. (To make sure that you are making a change you can use Narrator to hear what is happening even if you can't see it. Press Win+Ctrl+Enter to start Narrator. E.g. to switch from PC Screen Only to Second Screen Only you could press Win+P, End, Enter.) Fortunately doing either of these things makes the video system try again but sometimes it takes more than one try. Another quirk to be aware of is that there is a ridiculously short wait for a response to the Keep this...? prompt. So, if you didn't see it or couldn't respond in time it could look as if the other monitor could still not be used.
FYI
Robert Aldwinckle