As I recall, Spock says he (Kirk) took the test "three times", and therefore did face the real test twice. Since there can be no "winning" of the scenario -- normally -- I always figured this meant that cadets who were dissatisfied with their own performance could opt to re-take it. Indeed, the question of how many times a candidate chooses to subject themselves to a no-win scenario, and their reasons for doing so, might very well be part of what the Academy evaluates.
I think that’s a well stated response. What I would question is whether it would be a good thing to have someone take the test five times, fail miserably on four of them, then pass once and be considered a good candidate for leadership.
I would have some serious concerns over that candidate.
There is still the question in my mind, what value a test can have if you know from the onset that you cannot win.