I had a similar problem with my laptop connected to a Dell dock with two external monitors.
I updated all the Windows drivers, did a firmware update for my laptop, shutdown/unplugged/replugged everything, tried using my personal docking station (which is the same model as the one I assumed was no longer working), and still my external monitors would not load. I could see them in the Device Manager! And all of the other things plugged into the docking station worked fine. So I thought to check one more thing - the Intel Graphics Command Center. And there I found that the external monitors had been set to "disabled"!!! So I enabled them et voila! Why would the Windows update disable the monitors?? SO FRUSTRATING!