{"ID":2850896,"CreatedAt":"2026-06-01T04:54:23.091178241Z","UpdatedAt":"2026-06-01T04:54:23.091178241Z","DeletedAt":null,"paper_url":"https://arxiv.org/abs/2510.22085","arxiv_id":"2510.22085","title":"Jailbreak Mimicry: Automated Discovery of Narrative-Based Jailbreaks for Large Language Models","abstract":"Large language models (LLMs) remain vulnerable to sophisticated prompt engineering attacks that exploit contextual framing to bypass safety mechanisms, posing significant risks in cybersecurity applications. We introduce Jailbreak Mimicry, a systematic methodology for training compact attacker models to automatically generate narrative-based jailbreak prompts in a one-shot manner. Our approach transforms adversarial prompt discovery from manual craftsmanship into a reproducible scientific process, enabling proactive vulnerability assessment in AI-driven security systems. Developed for the OpenAI GPT-OSS-20B Red-Teaming Challenge, we use parameter-efficient fine-tuning (LoRA) on Mistral-7B with a curated dataset derived from AdvBench, achieving an 81.0% Attack Success Rate (ASR) against GPT-OSS-20B on a held-out test set of 200 items. Cross-model evaluation reveals significant variation in vulnerability patterns: our attacks achieve 66.5% ASR against GPT-4, 79.5% on Llama-3 and 33.0% against Gemini 2.5 Flash, demonstrating both broad applicability and model-specific defensive strengths in cybersecurity contexts. This represents a 54x improvement over direct prompting (1.5% ASR) and demonstrates systematic vulnerabilities in current safety alignment approaches. Our analysis reveals that technical domains (Cybersecurity: 93% ASR) and deception-based attacks (Fraud: 87.8% ASR) are particularly vulnerable, highlighting threats to AI-integrated threat detection, malware analysis, and secure systems, while physical harm categories show greater resistance (55.6% ASR). We employ automated harmfulness evaluation using Claude Sonnet 4, cross-validated with human expert assessment, ensuring reliable and scalable evaluation for cybersecurity red-teaming. Finally, we analyze failure mechanisms and discuss defensive strategies to mitigate these vulnerabilities in AI for cybersecurity.","short_abstract":"Large language models (LLMs) remain vulnerable to sophisticated prompt engineering attacks that exploit contextual framing to bypass safety mechanisms, posing significant risks in cybersecurity applications. We introduce Jailbreak Mimicry, a systematic methodology for training compact attacker models to automatically g...","url_abs":"https://arxiv.org/abs/2510.22085","url_pdf":"https://arxiv.org/pdf/2510.22085v1","authors":"[\"Pavlos Ntais\"]","published":"2025-10-24T23:53:16Z","proceeding":"cs.CR","tasks":"[\"cs.CR\",\"cs.AI\",\"cs.CL\",\"cs.LG\"]","methods":"[\"Large Language Model\",\"Language Model\",\"LoRA\"]","has_code":false}