This usually happens if the motor board is faulty, communication initialization will fail and get the Arduino stuck. This is really easy to check when this happens, simply removing the shield from the Arduino will let it instantly connect,

Arduino is plugged right into the PC, no USB hub. When plugged into PC, under Device Manager-Ports Arduino shows up as Arduino COM4.

Going into SimHub under Arduino-My Hardware-open Arduin setup tool, I can see Arduino COM4 in serial port and sketch uploads successful without issue.

Everything seems to be set up correctly, the sketch uploads without issue, and drivers seem to be UpToDate and correct. Chip sets also appear to be accurate.

The issue however is under Arduino-My Hardware, in the middle of the screen you'll see "Single Arduino Settings" and next to it says "Not Connected". Below that You'll see "Devices Scan", and it will rotate between "Hello", "Hello (sending)", and "Unrecognize". For whatever reason it doesn't seem to be recognizing the Arduino and motor shield, and therefore won't connect.

Has anyone else encountered this, and if so, what was the fix?