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JailbreakOPT introduces a tool-assisted framework that frames prompt selection as a contextual bandit problem to enhance iterative jailbreak attacks on LLMs. By organizing atomic prompts into a library and using Thompson sampling for exploration, the method achieves higher attack success rates with fewer queries than existing baselines. This work underscores the evolving sophistication of adversarial techniques and highlights the need for more robust safety mechanisms against adaptive, tool-mediated attacks.
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JailbreakOPT: Tool-Assisted Iterative Jailbreak Prompt Optimization

arXiv2 min read

arXiv:2606.11425v1 Announce Type: cross Abstract: 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.

Abstract: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.

Cryptography and Security (cs.CR); Artificial Intelligence (cs.AI)

arXiv:2606.11425 [cs.CR]

(or arXiv:2606.11425v1 [cs.CR] for this version)

https://doi.org/10.48550/arXiv.2606.11425 Focus to learn more arXiv-issued DOI via DataCite (pending registration)

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Full text under the publisher's open licence · 252 words