I experience this problem at least once per week. It's completely ludicrous. I switched from a laptop to a Surface Pro 3 as my full time professional work device and I totally regret it. The amount of time that I spend trouble shooting makes me furious.
In regard to the monitors not being recognized, this often occurs when I lock my desktop (e.g. Windows + L) and leave my desk to go to a meeting. I come back and, to my chagrin, the monitors are not working and then I go through a series of trouble shooting
steps which includes:
(1) rebooting
(2) disconnecting the multi-monitor adapter from the docking station
(3) disconnecting the power supply to the docking station.
Sometimes one or another of these steps works, and other times none of the steps work. I can't figure out how/why.
And this isn't the only problem with this device. When I lock the device (again, Windows + L), it automatically goes to sleep within a few seconds/minutes. But then sometimes I can't get it to turn back on. I hit the power button briefly, and sometimes
it works, but other times it doesn't. Then I tap some keys on my keyboard, and sometimes it works, but other times it doesn't. Then I move my mouse around, and sometimes it works, but other times it doesn't. Then I hit the Windows button, and sometimes
it works, but other times it doesn't. Again, I can't understand why/how any one of these actions sometimes works and when it doesn't.
And then the resolution between the docked device (which acts as monitor #3) and the other connected monitors (which act as #1 and #2) is so different that one or the other of them is basically unreadable (e.g. if the docked Surface Pro 3 is at the correct
resolution, then connected monitors #1 and #2 have resolution that is gigantic; if connected monitors #1 and #2 are at the correct resolution, then the Surface Pro 3 screen is tiny).
If anybody asked me my opinion about this device, I'd say that its only benefit (as compared to a laptop) is its light weight. Otherwise it's a complete nightmare. And now, I've lost another 10 minutes of productivity vis-a-vis this rant!