Self-play red-teaming improves language-model safety by pitting attacker and defender roles against each other in a zero-sum game. However, real adversaries increasingly use mosaic attacks: multi-turn sequences whose individual fragments are innocuous in isolation yet assemble into a harmful payload. We develop a theory of mosaic defense that characterizes what is required to prevent such attacks without sacrificing helpfulness. We first show that no fixed bounded window of recent prompts is sufficient in general: safety-relevant information may occur arbitrarily far back in the interaction. We formalize a watchman, an online state mechanism that carries this information forward, and show that under explicit assumptions it enables zero-failure defense with positive benign helpfulness. Under stronger conditions, it is also optimal among zero-failure defenders. An exact watchman may nevertheless require exponentially many states, while exact maliciousness detection can require exponentially many queries in an unstructured black-box model. These state and query lower bounds do not by themselves imply hard learning: the construction underlying the state lower bound is efficiently learnable from labeled examples, whereas certifying worst-case safety can require substantially more information under restricted access. We also show that self-play equilibrium alone does not certify usefulness, motivating a constrained formulation that maximizes worst-case benign helpfulness among zero-failure defenders. Empirically, training role-specific attacker and defender LoRA adapters over frozen LLMs via multi-turn self-play strengthens both roles: attackers become more effective at eliciting harmful responses, while defenders become more robust to attack, with improvements also observed on unseen attack objectives.

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