Why Formal Monitors Fail: Attack Distribution Entropy as a Coverage Bound for LTL-Based LLM Agent Safety

Abstract

Runtime safety monitors based on Linear Temporal Logic (LTL) and finite automata (FSA) are increasingly deployed to intercept unsafe tool-call sequences in LLM agents. Yet the same monitor achieves 68-75% attack coverage on some model architectures and near-zero on others, with no explanation from capability scores, training data, or prompt design. We provide the missing theory. We prove that the recall of any fixed-invariant FSA monitor is bounded above by the concentration of the attack distribution: the fraction of attacks covered by the k most frequent trigger-completion patterns. When attacks concentrate (low Shannon entropy), a small fixed invariant set achieves high recall; when they disperse across many structurally distinct patterns (high entropy), no fixed invariant set of tractable size can, regardless of how the invariants were derived. We validate this entropy-coverage bound across eight frontier LLM architectures. GPT-class and DeepSeek backends yield highly concentrated attacks (H ~ 0.24 bits; one pattern covers 96%), explaining 68-75% recall; Gemini variants yield high-entropy distributions (H ~ 2.81 bits; 7 clusters each<= 7%), explaining near-zero recall (6-13%), invariant to architecture-matched retraining. Entropy accounts for 76% of variance in coverage (Pearson r = -0.87, p = 0.005, 95% CI [-0.98, -0.78]), holding under leave-one-out (r in [-0.91, -0.82]). We introduce a pre-deployment entropy test that predicts monitor coverage from a small attack sample, enabling architecture-aware monitor selection before deployment. The bound and test are architecture-agnostic and apply to any FSA-based runtime monitor over discrete action sequences.