CySecBench: Generative AI-based CyberSecurity-focused Prompt Dataset for Benchmarking Large Language Models
On the map: LLM safety and security → Jailbreaking
Abstract (arXiv)
Numerous studies have investigated methods for jailbreaking Large Language Models (LLMs) to generate harmful content. Typically, these methods are evaluated using datasets of malicious prompts designed to bypass security policies established by LLM providers. However, the generally broad scope and open-ended nature of existing datasets can complicate the assessment of jailbreaking effectiveness, particularly in specific domains, notably cybersecurity. To address this issue, we present and publicly release CySecBench, a comprehensive dataset containing 12662 prompts specifically designed to evaluate jailbreaking techniques in the cybersecurity domain. The dataset is organized into 10 distinct attack-type categories, featuring close-ended prompts to enable a more consistent and accurate assessment of jailbreaking attempts. Furthermore, we detail our methodology for dataset generation and filtration, which can be adapted to create similar datasets in other domains. To demonstrate the utility of CySecBench, we propose and evaluate a jailbreaking approach based on prompt obfuscation. Our experimental results show that this method successfully elicits harmful content from commercial black-box LLMs, achieving Success Rates (SRs) of 65% with ChatGPT and 88% with Gemini; in contrast, Claude demonstrated greater resilience with a jailbreaking SR of 17%. Compared to existing benchmark approaches, our method shows superior performance, highlighting the value of domain-specific evaluation datasets for assessing LLM security measures. Moreover, when evaluated using prompts from a widely used dataset (i.e., AdvBench), it achieved an SR of 78.5%, higher than the state-of-the-art methods.
Key facts. Cited by 10 papers in the map (data through 7 Oct 2026). Placed in Jailbreaking, one of 12 directions in LLM safety and security. First posted on arXiv 2 Jan 2025.
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Citing papers per year: 2025: 5; 2026: 5.
10 papers.
- 2025Frontier AI's Impact on the Cybersecurity Landscapecited by 21
- 2025PurpCode: Reasoning for Safer Code Generationcited by 17
- 2025Prompt, Divide, and Conquer: Bypassing Large Language Model Safety Filters via Segmented and Distributed Prompt Processingcited by 5
- 2025Jailbreaking Large Language Models Through Content Concretizationcited by 2
- 2025Beyond Context: Large Language Models' Failure to Grasp Users' Intentcited by 1
- 2026A Systematic Review of Algorithmic Red Teaming Methodologies for Assurance and Security of AI Applicationscited by 1
- 2026Refusal Evaluation in Coding LLMs and Code Agents: A Systematic Review of Thirteen Malicious-Code Prompt Corpora (2023-2025)cited by 1
- 2026LLM Security and Safety: Insights from Homotopy-Inspired Prompt Obfuscationcited by 0
- 2026Code as a Weapon: A Consensus-Labeled Prompt Bank for Measuring Coding-Model Compliance with Malicious-Code Requestscited by 0
- 2026AlcaTRAz - Anchored Tree-Rule Defense Against Jailbreakscited by 0
- 2026AlcaTRAz - Anchored Tree-Rule Defense Against Jailbreaks3 Sep 2026
- 2026Code as a Weapon: A Consensus-Labeled Prompt Bank for Measuring Coding-Model Compliance with Malicious-Code Requests27 May 2026
- 2026Refusal Evaluation in Coding LLMs and Code Agents: A Systematic Review of Thirteen Malicious-Code Prompt Corpora (2023-2025)19 May 2026
- 2026A Systematic Review of Algorithmic Red Teaming Methodologies for Assurance and Security of AI Applications24 Feb 2026
- 2026LLM Security and Safety: Insights from Homotopy-Inspired Prompt Obfuscation20 Jan 2026
- 2025Beyond Context: Large Language Models' Failure to Grasp Users' Intent24 Dec 2025
- 2025Jailbreaking Large Language Models Through Content Concretization16 Sep 2025
- 2025PurpCode: Reasoning for Safer Code Generation25 Jul 2025
- 2025Frontier AI's Impact on the Cybersecurity Landscape7 Apr 2025
- 2025Prompt, Divide, and Conquer: Bypassing Large Language Model Safety Filters via Segmented and Distributed Prompt Processing27 Mar 2025