Seems the beveled edge on the display port connector (why MS why?) is causing people problems with standard display port to DVI connections. Thinking about USB 3.0 if it works.
The answer is yes. The other answer is just trim the collar of the adapter. I did this with a cheap micro to HDMI cable and it took about 30 seconds. It went from not working to working just that quick.
Thinking about picking up a Toshiba Dynadock Docking Station for $130 bucks. Seems pricey but you can run up to 2 secondary monitors and all your peripherals off a single USB 3.0 connection. One plug and you are golden to run 2 monitors, mouse, keyboard, external speakers, etc.