STM32 - Problem debugging using openocd and st-link
So I figured out my problem... 

Naively I believed the JTAG connector (via the st-link v2) was enough to power the board. I'm guessing trying to run the code (and blink the LED) while only powering the board through the JTAG pins could not supply enough current and the board kept resetting (hence the JTAG connection would break).

Long story short, ensure the USB cable is plugged into the board (and a power source) to power the board.