This all reminds me of the Kobayashi_Maru for some reason
James T. Kirk took the test three times while he was at Starfleet Academy. Prior to his third attempt, Kirk surreptitiously reprogrammed the simulator so that it was possible to win -- which he did, though we are not told exactly how. He justified it by arguing that putting cadets in a no-win situation was cheating, and so he had to cheat in return. He received a commendation for original thinking.
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