PrefixGuard: From LLM-Agent Traces to Online Failure-Warning Monitors

TL;DR

PrefixGuard is a framework for creating online failure-warning monitors for LLM agents, using trace analysis and supervised learning to improve early detection of failures in tool-using tasks.

Contribution

It introduces a novel trace-to-monitor framework with an offline induction step and supervised training, improving early failure detection over raw text controls.

Findings

PrefixGuard monitors achieve high AUPRC scores across multiple benchmarks.

Monitors outperform raw-text controls by an average of +0.137 AUPRC.

Finite-state automata remain compact on some benchmarks but expand on others.

Abstract

Large language model (LLM) agents now execute long, tool-using tasks where final outcome checks can arrive too late for intervention. Online warning requires lightweight prefix monitors over heterogeneous traces, but hand-authored event schemas are brittle and deployment-time LLM judging is costly. We introduce PrefixGuard, a trace-to-monitor framework with an offline StepView induction step followed by supervised monitor training. StepView induces deterministic typed-step adapters from raw trace samples, and the monitor learns an event abstraction and prefix-risk scorer from terminal outcomes. Across WebArena, $\tau^2$-Bench, SkillsBench, and TerminalBench, the strongest PrefixGuard monitors reach 0.900/0.710/0.533/0.557 AUPRC. Using the strongest backend within each representation, they improve over raw-text controls by an average of +0.137 AUPRC. LLM judges remain substantially weaker under the same prefix-warning protocol. We also derive an observability ceiling on score-based area under the precision-recall curve (AUPRC) that separates monitor error from failures lacking evidence in the observed prefix. For finite-state audit, post-hoc deterministic finite automaton (DFA) extraction remains compact on WebArena and $\tau^2$-Bench (29 and 20 states) but expands to 151 and 187 states on SkillsBench and TerminalBench. Finally, first-alert diagnostics show that strong ranking does not imply deployment utility: WebArena ranks well yet fails to support low-false-alarm alerts, whereas $\tau^2$-Bench and TerminalBench retain more actionable early alerts. Together, these results position PrefixGuard as a practical monitor-synthesis recipe with explicit diagnostics for when prefix warnings translate into actionable interventions.