I suspect it is not that it took special computer savvy to reprogram the computer, but rather the will and guts to actually do it, and exactly what to do to make it work, and then not get caught.
The test wasn’t devised to see how you win. It was devised to see how people held up under circumstances that led to defeat. This is a critical aspect of leadership. That’s an important thing to know, if you’re actually going to never give up, not lose your ability to think on your feet, and avoid defeat if at all possible.
Kirk circumvented this process. He was never evaluated in this manner. If that was a prerequisite, then he received preferential treatment by being allowed to pass without taking the test.