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

Penetration testing is essential to securing modern web infrastructures, yet traditional manual methods struggle to keep pace with their scale and complexity. Large Language Models (LLMs) offer new opportunities for automating these tasks, but existing approaches face two persistent challenges: hallucination of technical entities and insufficient long-term contextual memory. To address these issues, we present APT-Agent, a fully automated LLM-driven penetration testing framework that systematically orchestrates reconnaissance, exploitation, and exfiltration. APT-Agent introduces a hybrid rectification module to recover hallucinated commands and a command-specific memory architecture to preserve operational context across multi-step attack sequences. We evaluate our APT-Agent on Metasploitable 2 against seven vulnerable services spanning web, database, and network protocols. APT-Agent achieves an 84.29% end-to-end exploitation success rate, compared to 48.57% (Script Kiddie) and 18.57% (PentestGPT) under matched conditions. By reducing cognitive burden and minimizing reliance on human intervention, APT-Agent represents a step toward scalable, reliable, and cognitively efficient automation for penetration testing.

Nowadays, the autonomous execution of cyberattacks capable of causing substantial real-world harm is widely regarded as one of the critical red lines that frontier AI systems must not cross. Within this broader red-line scenario, autonomous penetration represents a core enabling capability and subtask: the ability of LLM-powered AI systems to independently conduct adversarial operations against a target server without human intervention, identify and exploit vulnerabilities, and obtain unauthorized access or control. A growing body of work has sought to assess the autonomous penetration capabilities of AI systems. However, existing evaluations often employ opaque methodologies, rely on unrealistic or overly simplified penetration-testing scenarios, or provide LLMs with excessive prior knowledge and task-specific guidance, and cannot accurately capture the extent to which modern AI systems can autonomously perform this core capability within broader high-impact cyberattack scenarios. To address these limitations, we construct a new autonomous penetration evaluation framework consisting of two components: target servers and agent scaffolding. Specifically, on the target-server side, we design two levels of target environments based on the number of secure services without known vulnerabilities deployed alongside a vulnerable service: Tier1 (one secure service) and Tier2 (three secure services), resulting in a total of 300 target servers. Meanwhile, the agent scaffolding adopts a general-purpose agent architecture equipped with a set of general-purpose cybersecurity tools, without any target-specific prior knowledge. We evaluate 19 open-weight and proprietary LLMs, and find that current models achieve penetration success rates ranging from 10.7% to 69.3%. Moreover, we observe that autonomous penetration capability continues to improve alongside advances in overall model capability.

LLM-driven automated penetration testing agents are typically evaluated against static targets that neither detect nor respond to attacks, so their behavior under intelligent defense remains untested. The causal consistency of multi-step attack chains likewise hinges on unstable LLM reasoning, and agent decisions remain opaque to human analysts. These three shortcomings, in realism, consistency, and auditability, are usually patched in isolation. We present ZERO-APT, a turn-based attacker-defender-judge framework that addresses them within a single architecture. For realism, ZERO-APT embeds a configurable LLM Defender that consumes Sysmon telemetry and detects attacks in real time, exposing the attacker to a live opponent rather than a passive target. For consistency, three architectural mechanisms move causal consistency from unstable LLM reasoning into enforced system architecture: separation of planning from execution, multi-dimensional ReAct feedback, and a hard-constraint-filtered action library. For auditability, a dedicated Judge agent adjudicates each round, maintains global state, and emits structured post-hoc CTI reports that make every decision traceable. We evaluate a Windows Server 2022 post-exploitation prototype across five scenarios with three Defender configurations. ZERO-APT reaches 79% attack success rate (Aurora 22%, PentestGPT 39%), a Causal Consistency Score of 0.860 (Aurora 0.930, Claude Code 0.520), and end-to-end decision auditability through structured CTI reports. We release the benchmark to support evaluation of penetration agents under intelligent defense.