Benchmarking Practices in LLM-driven Offensive Security: Testbeds, Metrics, and Experiment Design
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Abstract (arXiv)
Large Language Models (LLMs) have emerged as a powerful approach for driving offensive penetration-testing tooling. Due to the opaque nature of LLMs, empirical methods are typically used to analyze their efficacy. The quality of this analysis is highly dependent on the chosen testbed, captured metrics and analysis methods employed. This paper analyzes the methodology and benchmarking practices used for evaluating Large Language Model (LLM)-driven attacks, focusing on offensive uses of LLMs in cybersecurity. We review 19 research papers detailing 18 prototypes and their respective testbeds. We detail our findings and provide actionable recommendations for future research, emphasizing the importance of extending existing testbeds, creating baselines, and including comprehensive metrics and qualitative analysis. We also note the distinction between security research and practice, suggesting that CTF-based challenges may not fully represent real-world penetration testing scenarios.
Key facts. Cited by 14 papers in the map (data through 14 Oct 2026). Builds on 24 of its 46 references that are in the map. First posted on arXiv 14 Apr 2025.
Builds on
24 of 46 references.
References · 24
- 2023Large Language Modelscited by 780
- 2023A Survey on Large Language Model (LLM) Security and Privacy: The Good, the Bad, and the Uglycited by 387
- 2023Purple Llama CyberSecEval: A Secure Coding Benchmark for Language Modelscited by 138
- 2024LLM Agents can Autonomously Exploit One-day Vulnerabilitiescited by 128
- 2024AutoAttacker: A Large Language Model Guided System to Implement Automatic Cyber-attackscited by 96
- 2024Teams of LLM Agents can Exploit Zero-Day Vulnerabilitiescited by 95
- 2024NYU CTF Bench: A Scalable Open-Source Benchmark Dataset for Evaluating LLMs in Offensive Securitycited by 93
- 2024CyberSecEval 2: A Wide-Ranging Cybersecurity Evaluation Suite for Large Language Modelscited by 89
- 2023Getting pwn'd by AI: Penetration Testing with Large Language Modelscited by 83
- 2024Large Language Models for Cyber Security: A Systematic Literature Reviewcited by 68
- 2024CYBERSECEVAL 3: Advancing the Evaluation of Cybersecurity Risks and Capabilities in Large Language Modelscited by 58
- 2024HackSynth: LLM Agent and Evaluation Framework for Autonomous Penetration Testingcited by 37
12 more
- 2024An Empirical Evaluation of LLMs for Solving Offensive Security Challengescited by 35
- 2024A Comprehensive Overview of Large Language Models (LLMs) for Cyber Defences: Opportunities and Directionscited by 33
- 2025VulnBot: Autonomous Penetration Testing for A Multi-Agent Collaborative Frameworkcited by 31
- 2024PenHeal: A Two-Stage LLM Framework for Automated Pentesting and Optimal Remediationcited by 30
- 2023LLMs as Hackers: Autonomous Linux Privilege Escalation Attackscited by 27
- 2024AutoPenBench: Benchmarking Generative Agents for Penetration Testingcited by 21
- 2025Can LLMs Hack Enterprise Networks? Autonomous Assumed Breach Penetration-Testing Active Directory Networkscited by 12
- 2024Towards Automated Penetration Testing: Introducing LLM Benchmark, Analysis, and Improvementscited by 11
- 2025RapidPen: Fully Automated IP-to-Shell Penetration Testing with LLM-based Agentscited by 11
- 2024Review of Generative AI Methods in Cybersecuritycited by 9
- 2023Understanding Hackers' Work: An Empirical Study of Offensive Security Practitionerscited by 8
- 2024AutoPT: How Far Are We from the End2End Automated Web Penetration Testing?cited by 8
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Citing papers per year: 2025: 1; 2026: 13.
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- 2026Autonomous Agents on Blockchains: Standards, Execution Models, and Trust Boundariescited by 13
- 2026ZeroDayBench: Evaluating LLM Agents on Unseen Zero-Day Vulnerabilities for Cyberdefensecited by 4
- 2026CTFExplorer: Evaluating LLM Offensive Agents Through Multi-Target Web CTF Benchmarkingcited by 3
- 2025Cybersecurity AI: Evaluating Agentic Cybersecurity in Attack/Defense CTFscited by 1
- 2026CritBench: A Framework for Evaluating Cybersecurity Capabilities of Large Language Models in IEC 61850 Digital Substation Environmentscited by 1
- 2026How Reliable Are AI Attackers Against a Fixed Vulnerable Target? A 400-Run Empirical Study of LLM Penetration Testing Consistencycited by 1
- 2026Decoupling Reconnaissance and Exploitation: Measuring the Capability Boundaries of LLM-Based Web Penetration Testingcited by 1
- 2026How Do LLM Agents Actually Get the Flag? Trace-Level Provenance for Agentic Offensive Security Evaluationcited by 1
- 2026Can AI Lower the Barrier to Cybersecurity? A Human-Centered Mixed-Methods Study of Novice CTF Learningcited by 0
- 2026From Controlled to the Wild: Evaluation of Pentesting Agents for the Real-Worldcited by 0
- 2026Determinants and Limits of LLM Security-Tool Orchestration: A Study with HexStrike-AIcited by 0
- 2026Evaluating Agentic Learning Harness Capabilities Without Labels via the Scaling Hypothesiscited by 0
- 2026Does AI Help Cyber Attackers or Defenders? Evidence from Nonpublic Vulnerabilities and Subsequent Attacks5 Oct 2026
- 2026Toward Secure AI-Powered Penetration Testing Agents: Security Threats, Guardrails, and Architectural Perspectives15 Sep 2026
- 2026How Do LLM Agents Actually Get the Flag? Trace-Level Provenance for Agentic Offensive Security Evaluation26 Aug 2026
- 2026Evaluating Agentic Learning Harness Capabilities Without Labels via the Scaling Hypothesis11 Aug 2026
- 2026Determinants and Limits of LLM Security-Tool Orchestration: A Study with HexStrike-AI3 Jul 2026
- 2026Decoupling Reconnaissance and Exploitation: Measuring the Capability Boundaries of LLM-Based Web Penetration Testing24 Jun 2026
- 2026How Reliable Are AI Attackers Against a Fixed Vulnerable Target? A 400-Run Empirical Study of LLM Penetration Testing Consistency28 May 2026
- 2026From Controlled to the Wild: Evaluation of Pentesting Agents for the Real-World11 May 2026
- 2026CritBench: A Framework for Evaluating Cybersecurity Capabilities of Large Language Models in IEC 61850 Digital Substation Environments7 Apr 2026
- 2026ZeroDayBench: Evaluating LLM Agents on Unseen Zero-Day Vulnerabilities for Cyberdefense2 Mar 2026
- 2026Can AI Lower the Barrier to Cybersecurity? A Human-Centered Mixed-Methods Study of Novice CTF Learning20 Feb 2026
- 2026CTFExplorer: Evaluating LLM Offensive Agents Through Multi-Target Web CTF Benchmarking8 Feb 2026
- 2026Autonomous Agents on Blockchains: Standards, Execution Models, and Trust Boundariescited by 13
- 2026ZeroDayBench: Evaluating LLM Agents on Unseen Zero-Day Vulnerabilities for Cyberdefensecited by 4
- 2026CTFExplorer: Evaluating LLM Offensive Agents Through Multi-Target Web CTF Benchmarkingcited by 3
- 2025Cybersecurity AI: Evaluating Agentic Cybersecurity in Attack/Defense CTFscited by 1
- 2026How Do LLM Agents Actually Get the Flag? Trace-Level Provenance for Agentic Offensive Security Evaluationcited by 1
- 2026Can AI Lower the Barrier to Cybersecurity? A Human-Centered Mixed-Methods Study of Novice CTF Learningcited by 0
- 2026From Controlled to the Wild: Evaluation of Pentesting Agents for the Real-Worldcited by 0
- 2026Determinants and Limits of LLM Security-Tool Orchestration: A Study with HexStrike-AIcited by 0
- 2026Evaluating Agentic Learning Harness Capabilities Without Labels via the Scaling Hypothesiscited by 0
- 2026Toward Secure AI-Powered Penetration Testing Agents: Security Threats, Guardrails, and Architectural Perspectivescited by 0
- 2026Toward Secure AI-Powered Penetration Testing Agents: Security Threats, Guardrails, and Architectural Perspectives15 Sep 2026
- 2026How Do LLM Agents Actually Get the Flag? Trace-Level Provenance for Agentic Offensive Security Evaluation26 Aug 2026
- 2026Evaluating Agentic Learning Harness Capabilities Without Labels via the Scaling Hypothesis11 Aug 2026
- 2026Determinants and Limits of LLM Security-Tool Orchestration: A Study with HexStrike-AI3 Jul 2026
- 2026From Controlled to the Wild: Evaluation of Pentesting Agents for the Real-World11 May 2026
- 2026ZeroDayBench: Evaluating LLM Agents on Unseen Zero-Day Vulnerabilities for Cyberdefense2 Mar 2026
- 2026Can AI Lower the Barrier to Cybersecurity? A Human-Centered Mixed-Methods Study of Novice CTF Learning20 Feb 2026
- 2026CTFExplorer: Evaluating LLM Offensive Agents Through Multi-Target Web CTF Benchmarking8 Feb 2026
- 2026Autonomous Agents on Blockchains: Standards, Execution Models, and Trust Boundaries8 Jan 2026
- 2025Cybersecurity AI: Evaluating Agentic Cybersecurity in Attack/Defense CTFs20 Oct 2025
- 2026CritBench: A Framework for Evaluating Cybersecurity Capabilities of Large Language Models in IEC 61850 Digital Substation Environmentscited by 1
- 2026How Reliable Are AI Attackers Against a Fixed Vulnerable Target? A 400-Run Empirical Study of LLM Penetration Testing Consistencycited by 1
- 2026Decoupling Reconnaissance and Exploitation: Measuring the Capability Boundaries of LLM-Based Web Penetration Testingcited by 1
- 2026Does AI Help Cyber Attackers or Defenders? Evidence from Nonpublic Vulnerabilities and Subsequent Attackscited by 0
- 2026Does AI Help Cyber Attackers or Defenders? Evidence from Nonpublic Vulnerabilities and Subsequent Attacks5 Oct 2026
- 2026Decoupling Reconnaissance and Exploitation: Measuring the Capability Boundaries of LLM-Based Web Penetration Testing24 Jun 2026
- 2026How Reliable Are AI Attackers Against a Fixed Vulnerable Target? A 400-Run Empirical Study of LLM Penetration Testing Consistency28 May 2026
- 2026CritBench: A Framework for Evaluating Cybersecurity Capabilities of Large Language Models in IEC 61850 Digital Substation Environments7 Apr 2026