Know Your Agent: Reconnaissance-Driven Pentesting of AI Agents

AI pentesting agents are increasingly credible as offensive security systems, but current benchmarks still provide limited guidance on which will perform best in real-world targets. Existing evaluation protocols assess and optimize for predefined goals such as capture-the-flag, remote code execution, exploit reproduction, or trajectory similarity, in simplified or narrow settings. These tools are valuable for measuring bounded capabilities, yet they do not adequately capture the complexity, open-ended exploration, and strategic decision-making required in realistic pentesting. In this paper, we present a practical evaluation protocol that shifts assessment from task completion to validated vulnerability discovery, allowing evaluation in sufficiently complex targets spanning multiple attack surfaces and vulnerability classes. The protocol combines structured ground-truth with LLM-based semantic matching to identify vulnerabilities, bipartite resolution to score findings under realistic ambiguity, continuous ground-truth maintenance, repeated and cumulative evaluation of stochastic agents, efficiency metrics, and reduced-suite selection for sustainable experimentation. This protocol extends the state of the art by enabling a more realistic, operationally informative comparison of AI pentesting agents. To enable reproducibility, we also release expert-annotated ground truth and code for the proposed evaluation protocol: https://github.com/ethiack/ethibench.

Agent benchmarks have become the de facto measure of frontier AI competence, guiding model selection, investment, and deployment. However, reward hacking, where agents maximize a score without performing the intended task, emerges spontaneously in frontier models without overfitting. We argue that benchmarks must be secure by design. From past incidents of reward hacks, we derive a taxonomy of eight recurring flaw patterns and compile them into the Agent-Eval Checklist for benchmark designers. We condense the insights into BenchJack, an automated red-teaming system that drives coding agents to audit benchmarks and identify possible reward-hacking exploits in a clairvoyant manner. Moreover, we extend BenchJack to an iterative generative-adversarial pipeline that discovers new flaws and patches them iteratively to improve benchmark robustness. We apply BenchJack to 10 popular agent benchmarks spanning software engineering, web navigation, desktop computing, and terminal operations. BenchJack synthesizes reward-hacking exploits that achieve near-perfect scores on most of the benchmarks without solving a single task, surfacing 219 distinct flaws across the eight classes. Moreover, BenchJack's extended pipeline reduces the hackable-task ratio from near 100% to under 10% on four benchmarks without fatal design flaws, fully patching WebArena and OSWorld within three iterations. Our results show that evaluation pipelines have not internalized an adversarial mindset, and that proactive auditing could help close the security gap for the fast-paced benchmarking space.

As AI systems gain increasing autonomy and execution capability, the number of discovered security vulnerabilities continues to rise. However, many of these vulnerabilities are not fundamentally novel, but instead reflect recurring classes of weaknesses long observed in prior computing systems. Execution-capable AI agents are effectively unbounded, self-modifying programs that interact extensively with multiple layers of the computing stack. This broad interaction surface imposes a significant security burden on developers, who must reason about and secure complex cross-layer behaviors. Prior research has primarily focused on vulnerabilities in open-source agents and agent frameworks. In contrast, it remains unclear whether proprietary agent systems -- developed under stricter coding standards and formal review processes -- exhibit similar security weaknesses. In this paper, we present findings from two penetration tests conducted in 2025 against proprietary agent products and evaluate whether the security posture of AI agents has improved since these assessments.