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We built an adaptive attacker that evolves its strategies over hundreds of rounds and tested it against nine defense configurations across more than 20,000 attacks. Every defense that relied on the model to protect itself eventually broke. The only defense that held was output filtering, which checks the model's responses via hardcoded rules in separate application code before they reach the user, achieving zero leaks across 15,000 attacks. These results demonstrate that security boundaries must be enforced in application code, not by the model being attacked. 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These results demonstrate that security boundaries must be enforced in application code, not by the model being attacked. 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