Guided Reasoning in LLM-Driven Penetration Testing Using Structured Attack Trees

Abstract

Recent advances in Large Language Models (LLMs) have driven interest in automating cybersecurity penetration testing workflows, offering the promise of faster and more consistent vulnerability assessment for enterprise systems. Existing LLM agents for penetration testing primarily rely on self-guided reasoning, which can produce inaccurate or hallucinated procedural steps. As a result, the LLM agent may undertake unproductive actions, such as exploiting unused software libraries or generating cyclical responses that repeat prior tactics. In this work, we propose a guided reasoning pipeline for penetration testing LLM agents that incorporates a deterministic task tree built from the MITRE ATT&CK Matrix, a proven penetration testing kll chain, to constrain the LLM's reaoning process to explicitly defined tactics, techniques, and procedures. This anchors reasoning in proven penetration testing methodologies and filters out ineffective actions by guiding the agent towards more productive attack procedures. To evaluate our approach, we built an automated penetration testing LLM agent using three LLMs (Llama-3-8B, Gemini-1.5, and GPT-4) and applied it to navigate 10 HackTheBox cybersecurity exercises with 103 discrete subtasks representing real-world cyberattack scenarios. Our proposed reasoning pipeline guided the LLM agent through 71.8\%, 72.8\%, and 78.6\% of subtasks using Llama-3-8B, Gemini-1.5, and GPT-4, respectively. Comparatively, the state-of-the-art LLM penetration testing tool using self-guided reasoning completed only 13.5\%, 16.5\%, and 75.7\% of subtasks and required 86.2\%, 118.7\%, and 205.9\% more model queries. This suggests that incorporating a deterministic task tree into LLM reasoning pipelines can enhance the accuracy and efficiency of automated cybersecurity assessments