# Using Large Language Models for Cybersecurity Capture-The-Flag Challenges and Certification Questions

arXiv: https://arxiv.org/abs/2308.10443 · HTML: https://mlsanity.com/paper/2308.10443/

## Key facts

- Cited by 23 papers in the map (data through 14 Oct 2026).
- Builds on 9 of its 18 references that are in the map.
- First posted on arXiv 21 Aug 2023.

## Builds on (most cited first, 9 of 9)

- [Attention Is All You Need](https://mlsanity.com/paper/1706.03762/) (2017)
- [Language Models are Few-Shot Learners](https://mlsanity.com/paper/2005.14165/) (2020)
- [PaLM: Scaling Language Modeling with Pathways](https://mlsanity.com/paper/2204.02311/) (2022)
- [Emergent Abilities of Large Language Models](https://mlsanity.com/paper/2206.07682/) (2022)
- [Extracting Training Data from Large Language Models](https://mlsanity.com/paper/2012.07805/) (2020)
- [Jailbroken: How Does LLM Safety Training Fail?](https://mlsanity.com/paper/2307.02483/) (2023)
- [From ChatGPT to ThreatGPT: Impact of Generative AI in Cybersecurity and Privacy](https://mlsanity.com/paper/2307.00691/) (2023)
- [Beyond the Safeguards: Exploring the Security Risks of ChatGPT](https://mlsanity.com/paper/2305.08005/) (2023)
- [Generating Phishing Attacks using ChatGPT](https://mlsanity.com/paper/2305.05133/) (2023)

## Built on by (most cited first, 23 of 23)

- [A Survey on Large Language Model (LLM) Security and Privacy: The Good, the Bad, and the Ugly](https://mlsanity.com/paper/2312.02003/) (2023)
- [Black-Box Access is Insufficient for Rigorous AI Audits](https://mlsanity.com/paper/2401.14446/) (2024)
- [AutoAttacker: A Large Language Model Guided System to Implement Automatic Cyber-attacks](https://mlsanity.com/paper/2403.01038/) (2024)
- [NYU CTF Bench: A Scalable Open-Source Benchmark Dataset for Evaluating LLMs in Offensive Security](https://mlsanity.com/paper/2406.05590/) (2024)
- [When LLMs Meet Cybersecurity: A Systematic Literature Review](https://mlsanity.com/paper/2405.03644/) (2024)
- [Large Language Models in Cybersecurity: State-of-the-Art](https://mlsanity.com/paper/2402.00891/) (2024)
- [Frontier AI's Impact on the Cybersecurity Landscape](https://mlsanity.com/paper/2504.05408/) (2025)
- [D-CIPHER: Dynamic Collaborative Intelligent Multi-Agent System with Planner and Heterogeneous Executors for Offensive Security](https://mlsanity.com/paper/2502.10931/) (2025)
- [A Framework for Evaluating Emerging Cyberattack Capabilities of AI](https://mlsanity.com/paper/2503.11917/) (2025)
- [Measuring and Augmenting Large Language Models for Solving Capture-the-Flag Challenges](https://mlsanity.com/paper/2506.17644/) (2025)
- [CRAKEN: Cybersecurity LLM Agent with Knowledge-Based Execution](https://mlsanity.com/paper/2505.17107/) (2025)
- [Towards Effective Offensive Security LLM Agents: Hyperparameter Tuning, LLM as a Judge, and a Lightweight CTF Benchmark](https://mlsanity.com/paper/2508.05674/) (2025)
- [Hackphyr: A Local Fine-Tuned LLM Agent for Network Security Environments](https://mlsanity.com/paper/2409.11276/) (2024)
- [A Survey of Large Language Models in Cybersecurity](https://mlsanity.com/paper/2402.16968/) (2024)
- [Dynamic Risk Assessments for Offensive Cybersecurity Agents](https://mlsanity.com/paper/2505.18384/) (2025)
- [Applying Refusal-Vector Ablation to Llama 3.1 70B Agents](https://mlsanity.com/paper/2410.10871/) (2024)
- [Hacking, The Lazy Way: LLM Augmented Pentesting](https://mlsanity.com/paper/2409.09493/) (2024)
- [Improving LLM Agents with Reinforcement Learning on Cryptographic CTF Challenges](https://mlsanity.com/paper/2506.02048/) (2025)
- [CyberLLMInstruct: A Pseudo-malicious Dataset Revealing Safety-performance Trade-offs in Cyber Security LLM Fine-tuning](https://mlsanity.com/paper/2503.09334/) (2025)
- [AI In Cybersecurity Education -- Scalable Agentic CTF Design Principles and Educational Outcomes](https://mlsanity.com/paper/2603.21551/) (2026)
- [CyberCertBench: Evaluating LLMs in Cybersecurity Certification Knowledge](https://mlsanity.com/paper/2604.20389/) (2026)
- [LISAA: A Framework for Large Language Model Information Security Awareness Assessment](https://mlsanity.com/paper/2411.13207/) (2024)
- [From Capabilities to Performance: Evaluating Key Functional Properties of LLM Architectures in Penetration Testing](https://mlsanity.com/paper/2509.14289/) (2025)

## Abstract (arXiv)

The assessment of cybersecurity Capture-The-Flag (CTF) exercises involves participants finding text strings or ``flags'' by exploiting system vulnerabilities. Large Language Models (LLMs) are natural-language models trained on vast amounts of words to understand and generate text; they can perform well on many CTF challenges. Such LLMs are freely available to students. In the context of CTF exercises in the classroom, this raises concerns about academic integrity. Educators must understand LLMs' capabilities to modify their teaching to accommodate generative AI assistance. This research investigates the effectiveness of LLMs, particularly in the realm of CTF challenges and questions. Here we evaluate three popular LLMs, OpenAI ChatGPT, Google Bard, and Microsoft Bing. First, we assess the LLMs' question-answering performance on five Cisco certifications with varying difficulty levels. Next, we qualitatively study the LLMs' abilities in solving CTF challenges to understand their limitations. We report on the experience of using the LLMs for seven test cases in all five types of CTF challenges. In addition, we demonstrate how jailbreak prompts can bypass and break LLMs' ethical safeguards. The paper concludes by discussing LLM's impact on CTF exercises and its implications.