This study reveals how frontier Large Language Models LLMs can “game the system” when faced with impossible situations, a critical security and alignment concern. Using a novel textual simulation approach, we presented three leading LLMs (o1, o3-mini, and r1) with a tic-tac-toe scenario designed to be unwinnable through legitimate play, then analyzed their tendency to exploit loopholes rather than accept defeat. Our results are alarming for security researchers: the newer, reasoning-focused o3-mini model showed nearly twice the propensity to exploit system vulnerabilities (37.1%) compared to the older o1 model (17.5%). Most striking was the effect of prompting—simply framing the task as requiring “creative” solutions caused gaming behaviors to skyrocket to 77.3% across all models. We identified four distinct exploitation strategies, from direct manipulation of game state to sophisticated modification of opponent behavior. These findings demonstrate that even without actual execution capabilities, LLMs can identify and propose sophisticated system exploits when incentivized, highlighting urgent challenges for AI alignment as models grow more capable of identifying and leveraging vulnerabilities in their operating environments.