TraceSafe: A Systematic Assessment of LLM Guardrails on Multi-Step Tool-Calling Trajectories

As Large Language Models (LLMs) evolve into autonomous agents that alter real-world states, ensuring operational safety across multi-step workflows has become a critical challenge. While recent work has moved beyond single-turn evaluation toward multi-turn paradigms, key limitations persist: step-level methods treat actions in isolation, missing how risks accumulate, while trajectory-level evaluations operate post-hoc, offering no opportunity for timely intervention. To address these limitations, we formalize Decoupled Proactive Safety Monitoring along three dimensions: whether to intervene, when to intervene, and what the risk is. We introduce PASTABench, a benchmark of 1,139 multi-turn trajectories spanning 5 risk categories and 13 subcategories. We further propose the Optimal Intervention Window (OIW), anchored by annotated Earliest-Signal and Trigger turns, to quantify intervention timeliness. Evaluation of 16 LLMs reveals that proactive intervention remains largely unsolved, with the best model achieving only 40.74% optimal-timing interventions. Fine-grained diagnosis further uncovers pervasive lexical overfitting: competitive safety scores of smaller models mask keyword hypersensitivity rather than genuine risk comprehension, as their proactive capability largely collapses once hazard vocabulary is neutralized.

Evaluating the safety of LLM-based agents is increasingly important because risks in realistic deployments often emerge over multi-step interactions rather than isolated prompts or final responses. Existing trajectory-level benchmarks remain limited by insufficient interaction diversity, coarse observability of safety failures, and weak long-horizon realism. We introduce ATBench, a trajectory-level benchmark for structured, diverse, and realistic evaluation of agent safety. ATBench organizes agentic risk along three dimensions: risk source, failure mode, and real-world harm. Based on this taxonomy, we construct trajectories with heterogeneous tool pools and a long-context delayed-trigger protocol that captures realistic risk emergence across multiple stages. The benchmark contains 1,000 trajectories (503 safe and 497 unsafe), averaging 9.01 turns and 3.95k tokens, with 1,954 invoked tools drawn from pools spanning 2,084 available tools. Data quality is supported by rule-based and LLM-based filtering plus full human audit. Experiments on frontier LLMs, open-source models, and specialized guard systems show that ATBench is challenging even for strong evaluators, while enabling taxonomy-stratified analysis, cross-benchmark comparison, and diagnosis of long-horizon failure patterns.

Tool-using LLM agents increasingly rely on external tools to make consequential decisions, yet most existing agent-security benchmarks and defenses implicitly assume that tool feedback is trustworthy once a tool has been selected. We study a different failure mode, cognitive poisoning, in which a malicious tool behaves plausibly during exploration, accumulates trust through benign-looking feedback, and becomes harmful only when hidden state conditions align with the final executable action. To study this setting, we construct TRUST-Bench, a task-conditioned benchmark of 1,970 hidden-trigger tool-compromise episodes with matched safe controls, introduce an asymmetric penalty metric, GuardedJoint, to better reflect real deployment risk, and present VISTA-Guard, a backbone-agnostic framework for final-action risk scoring. The core idea is to abstract multi-step tool interaction into structured environment variables that encode trust-formation dynamics and then score the risk of the final executable action from this trajectory-conditioned representation. Experiments show that prompt-centric heuristics, scalarized features, and zero-shot judges fail in this regime, whereas trajectory-aware final-action scoring yields strong in-domain discrimination and remains effective under balanced out-of-distribution transfer. Under GuardedJoint, VISTA-Guard reaches $84.2$ in-domain and $56.9$ on balanced out-of-distribution evaluation, while methods that optimize only one side of the safety--utility tradeoff collapse to zero. These findings support a broader view of agent security in black-box tool ecosystems: the decisive defense target is not local prompt text or tool descriptors alone, but the way trust is formed across the interaction trajectory and committed through the final action.