Organizations: aSchool of Cyber Science and Engineering, Sichuan University, Chengdu 610065, China · dCollege of Computer Science, Sichuan University, Chengdu 610065, China · aSchool of Cyber Science and Engineering, Sichuan University, Chengdu 610065, China bKey Laboratory of Data Protection and Intelligent Management (Sichuan University), Ministry of Education, Chengdu 610065, China
As LLMs continue to shape real-world applications, automated jailbreak generation becomes essential to reveal safety weaknesses and guide model improvement. Existing automatic jailbreak generation methods have not yet fully considered two important aspects: adaptability to evolving safety-finetuned models, which affects their effectiveness on newer model versions, and diversity in generated prompts, which can cause narrow or repetitive attack patterns. To address these issues, we propose EvoJail, an instruction-fusion-driven evolutionary jailbreak generation framework that formalizes jailbreak prompt generation as a multi-objective black-box optimization problem and leverages the principles of evolutionary algorithms to search for jailbreak prompts that can adapt across different model versions and exhibit diverse attack patterns. Specifically, EvoJail integrates jailbreak prompt generation into an iterative evolutionary loop, where at each iteration candidate prompts are evaluated directly against the target model and then selected and varied based on the target model's responses, enabling the generation process to continuously adapt to model updates. To enhance diversity, EvoJail introduces field-aware instruction fusion to construct diverse starting points and incorporates diversity-aware objectives into the evolutionary fitness function, guiding the search toward prompts with richer semantic variation, while further designing multi-level LLM-based mutation operators that modify prompt structures at different granularities to promote structural diversity throughout the evolutionary process. Results demonstrate that EvoJail has stronger adaptability and can achieve over 93% attack success rate and more than 5.6% improvement in diversity metrics over state-of-the-art methods.
Jailbreak attacks expose persistent safety weaknesses in large language models (LLMs), but existing stateless single-turn methods face a trade-off: hand-crafted prompts are expressive but static, while iterative prompt optimization can adapt but often relies on low-level mutations that require many target queries. We propose JailbreakOPT, a tool-assisted framework for improving iterative single-turn jailbreak prompt optimization. JailbreakOPT organizes diverse atomic jailbreak prompts into an attack tool library and composes them through a unified intra-episode optimization abstraction to generate stronger standalone attack prompts. To reuse experience across attack episodes, JailbreakOPT further frames tool selection as a contextual bandit problem and applies contextual Thompson sampling to guide exploration and exploitation based on past outcomes. Experiments across multiple target LLMs and attack goals show that JailbreakOPT improves attack success rate (ASR) while reducing the number of attacks until success (No.A) compared with atomic single-turn attacks and existing iterative optimization baselines. This paper may contain offensive or harmful content.
Jailbreak attacks -- adversarial prompts that bypass LLM alignment through purely linguistic manipulation -- pose a growing operational security threat, yet the field lacks large-scale, reproducible infrastructure for generating, categorizing, and evaluating them systematically. This paper addresses that gap with three contributions. (1) Large-scale compositional jailbreak dataset. We construct 114,000 adversarial prompts by applying 912 composing strategies to 125 harmful seed prompts from JailBreakV-28K. Every prompt is assigned to one of 14 cybersecurity attack categories (e.g., malware, phishing, privilege escalation) via a six-model majority-vote pipeline, and each strategy is ranked by effectiveness per category, enabling principled strategy selection grounded in concrete adversarial objectives. (2) Automated jailbreak generation. We instruction-fine-tune category-aware LLMs on Moderate and Optimal subsets, producing models that synthesize fluent jailbreak prompts from a harmful seed at inference time -- no templates, no gradient search. Our generators achieve perplexity 24-39 versus 40-140 for AutoDAN and AmpleGCG, with safety-filter evasion rates of 0.29-0.51 Mal (LlamaPromptGuard-2-86M), enabling controllable, scalable red-teaming under realistic adversarial conditions. (3) OPTIMUS: a training-free jailbreak evaluator. OPTIMUS is a continuous metric J(S,H) that jointly captures semantic similarity between the harmful seed and the jailbreak (S) and harmfulness probability (H) via calibrated penalty functions. Unlike binary attack success rate (ASR), OPTIMUS requires no task-specific training, generalizes across evolving strategies, and exposes a stealth-optimal regime (S*=0.57, H*=0.43) that ASR misses. Experiments across 114,000 prompts confirm that OPTIMUS separates Weak, Moderate, and Optimal jailbreaks with category-level evidence binary evaluation cannot supply.
LLMs are increasingly equipped with safety alignment mechanisms, yet recent studies demonstrate that they remain vulnerable to jailbreaking attacks that elicit harmful behaviors without explicit policy violations. While a growing body of work has explored automated jailbreak strategies, existing methods face several fundamental challenges, including the lack of systematic utilization of both successful and failed attack experiences, as well as the absence of principled mechanisms for composing and selecting reusable attack rules under diverse constraints. As a result, existing methods struggle to accumulate transferable knowledge over time and to reliably adapt attack strategies across different targets and evolving safety mechanisms. To address these issues, we propose a Self-Evolving Rule-Driven Training-Free Jailbreak (SRTJ) framework that systematically discovers, composes, and refines attack strategies through interaction and feedback, without updating model parameters. Specifically, SRTJ couples experience-driven attack generation with answer set programming (ASP)-based rule selection and constraint-aware composition, where iterative verifier feedback is leveraged to jointly refine successful strategies and analyze failure patterns. The resulting rule memory evolves in a hierarchical multi-level manner, explicitly organizing distilled attack knowledge into long-term, middle-term, and short-term rules, thereby capturing both stable transferable strategies and transient adaptive behaviors to effectively balance exploration and exploitation across attack attempts. Extensive experiments on mainstream jailbreak benchmark (HarmBench) demonstrate that SRTJ achieves strong and stable attack performance across different target LLMs, while exhibiting improved robustness and generalization compared to existing jailbreak methods. The code is available at https://github.com/TheSolkatt/SRTJ.