Beyond End-to-End Success: Diagnosing Failures in Long-Horizon Security LLM Agents

Long-horizon security LLM agents must carry information and decisions across many dependent interactions, where later actions often depend on services, state, or access discovered much earlier. This makes final task success difficult to interpret: an agent may fail before it ever reaches the point where the capability of interest can be exercised. We present a diagnostic methodology that instruments security tasks with checkpoints, separates failures before and after capability exposure, and uses controlled interventions to test suspected upstream bottlenecks. We evaluate the methodology across four task families involving delayed reuse of discovered information, reuse of observed state, recovery from failed strategies, and decision making after uncertain outcomes. On observed state reuse, checkpoint analysis shows that many Gemini 2.5 Flash failures occur before the model observes the state it is later expected to reuse. In a pre-specified 92-seed study, targeted protocol-disambiguation guidance increases state observation from 65.5\% under a matched non-guidance control message to 95.4\%. Repeating the same design with Gemini 3.7 Flash produces the opposite effect, while state observation no longer reliably predicts task completion. These results show that the dominant source of failure can shift across model generations, motivating evaluation that diagnoses where and why long-horizon security agents fail rather than relying only on aggregate task success.

Post-Hoc Trajectory-Risk Certification for Modular LLM-Based Security Agents

Autonomous security agents operate as staged pipelines, such as classifying network traffic and then attributing attacks to a specific technique. Split conformal prediction gives each stage finite-sample coverage, but deployment requires a trajectory-level guarantee across the full chain. These guarantees do not compose automatically when stages are independently trained and calibrated. Bonferroni allocation is distribution-free but conservative under correlated errors. We show that a natural pairwise-correlation extension to three or more stages is invalid because it gives a lower rather than an upper bound, and derive a valid spanning-tree alternative. We distinguish whether stages are dependent from whether an audit sample is large enough to certify that dependence, and give matching upper and information-theoretic lower sample-complexity bounds. We also show that coarse-to-fine label selection can create near-perfect measured correlation without learned dependence. On a two-stage intrusion-detection pipeline across 6 open LLMs and 2 datasets, removing this artifact reduces measured correlation from near 1 to 0-0.78. A direct audit of trajectory failure becomes 13.7% tighter than Bonferroni once the audit reaches the required sample size, but is worse when undersized. A modular certificate using per-stage certificates and a pairwise overlap bound yields a positive average gain of 0.6%, quantifying the cost of lacking joint access. Same-model, cross-model, and permuted-pairing tests show that residual dependence reflects shared sample difficulty, not shared model representations. Average trajectory coverage across 12 configurations is 92.7% +/- 2.4% at alpha = 0.10. Under cross-dataset deployment, single-step miscoverage reaches 100% even when accuracy remains 78%, showing that distribution shift destroys calibrated confidence before raw accuracy.

Beyond Success Rate: Cost-Aware Evaluation of Offensive and Defensive Security Agents

Security-agent evaluations commonly measure peak offensive capability under generous inference budgets, emphasizing vulnerability discovery, exploit development, penetration testing, and CTF completion. Such measurements are useful but incomplete: in operational security, every reasoning step, tool call, telemetry query, and enrichment request consumes budget. We evaluate language-model security agents through this cost-success lens on offensive Cybench challenges and defensive Splunk BOTS v1 investigation challenges. Instead of reporting only best-case success, we compare models at fixed cost levels and decompose performance by inference spend and tool spend. Our results show distinct scalingregimes for red- and blue-team tasks. Offensive CTF performance improves with additional test-time compute, and scaled open-weight models can approach frontier proprietary systems while remaining cost-competitive. Defensive SOC investigation does not scale in the same way: success depends more heavily on disciplined tool use, telemetry navigation, and selective enrichment than on raw reasoning budget alone. We argue that security-agent benchmarks should measure economic efficiency and operational fit alongside task success. Cost-aware, SOC-native evaluations provide a clearer picture of which models are practically useful today and where defensive agents still need to improve. We present an interactive website with our results https://evals.frontier.security.

Decoupling Reconnaissance and Exploitation: Measuring the Capability Boundaries of LLM-Based Web Penetration Testing

Large Language Models (LLMs) have shown promise for automated penetration testing, yet existing end-to-end black-box evaluations are highly susceptible to error cascading: failures in early reconnaissance can mask an agent's actual ability to exploit vulnerabilities. To more accurately characterize these capabilities, we propose a two-stage decoupled evaluation framework that separates exploit execution from reconnaissance. Using ground-truth injection and knowledge-driven ablation across 70 high-fidelity web vulnerability testbeds, our framework isolates exploitation performance from reconnaissance noise. We empirically evaluate five open-source penetration-testing agents, covering multiagent, monolithic, and graph-driven architectures, on a strictly aligned subset of 50 representative vulnerabilities. The results reveal a substantial capability gap. With accurate vulnerability context, agents achieve a functional success rate of up to 90.0%, whereas autonomous reconnaissance, measured by targeted vulnerability recall, plateaus at approximately 50.0%, primarily due to failures in parsing unstructured telemetry. Cross-architectural analysis further reveals distinct capability niches: multi-agent isolation is more effective for long-sequence interactions such as de-serialization, while monolithic and graph-driven designs perform better on short-chain injections and cross-session access-control vulnerabilities, respectively. This decoupled evaluation work provides a fine-grained benchmarking protocol and an empirical basis for designing next-generation automated offensive security agents.