I setup new Surface's where I work. So far they have all been Surface Pro 3 with the newer docking station. Frequently after plugging everything in, the external monitor doesn't connect. Sometimes unplugging and reconnecting the monitor cable either to the dock or directly to the Surface gets it to connect but more frequently I need to reseat the connection from the dock to the Surface to get it to connect. It seems that when I connect the dock cable to the Surface, it connects up more frequently if I put the connector in with the cable going up instead of down. Has any of you had this problem. I ran a pencil eraser over the gold connect pins like I use to do in the old days on plug in boards but it doesn't seem t be a dirty connector. It sure points to hardware but since it is doing it on all the new Surfaces I setup, it makes me think it could be software. I run updates, even right after I upgrade the OS to the Anniversary edition.