# JailbreakOPT: Tool-Assisted Iterative Jailbreak Prompt Optimization

arXiv: https://arxiv.org/abs/2606.11425 · HTML: https://mlsanity.com/paper/2606.11425/

## Key facts

- Cited by 1 papers in the map (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 35 of its 54 references that are in the map.
- First posted on arXiv 9 Jun 2026.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Builds on (most cited first, 30 of 35)

- [Qwen3 Technical Report](https://mlsanity.com/paper/2505.09388/) (2025)
- [Efficient Memory Management for Large Language Model Serving with PagedAttention](https://mlsanity.com/paper/2309.06180/) (2023)
- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [A Comprehensive Survey of Continual Learning: Theory, Method and Application](https://mlsanity.com/paper/2302.00487/) (2023)
- [AutoDAN: Generating Stealthy Jailbreak Prompts on Aligned Large Language Models](https://mlsanity.com/paper/2310.04451/) (2023)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [How Johnny Can Persuade LLMs to Jailbreak Them: Rethinking Persuasion to Challenge AI Safety by Humanizing LLMs](https://mlsanity.com/paper/2401.06373/) (2024)
- [GPTFUZZER: Red Teaming Large Language Models with Auto-Generated Jailbreak Prompts](https://mlsanity.com/paper/2309.10253/) (2023)
- [A Tutorial on Thompson Sampling](https://mlsanity.com/paper/1707.02038/) (2017)
- [GPT-4 Is Too Smart To Be Safe: Stealthy Chat with LLMs via Cipher](https://mlsanity.com/paper/2308.06463/) (2023)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [A Wolf in Sheep's Clothing: Generalized Nested Jailbreak Prompts can Fool Large Language Models Easily](https://mlsanity.com/paper/2311.08268/) (2023)
- [Jailbreak Attacks and Defenses Against Large Language Models: A Survey](https://mlsanity.com/paper/2407.04295/) (2024)
- [ArtPrompt: ASCII Art-based Jailbreak Attacks against Aligned LLMs](https://mlsanity.com/paper/2402.11753/) (2024)
- [AutoDAN-Turbo: A Lifelong Agent for Strategy Self-Exploration to Jailbreak LLMs](https://mlsanity.com/paper/2410.05295/) (2024)
- [Robust Prompt Optimization for Defending Language Models Against Jailbreaking Attacks](https://mlsanity.com/paper/2401.17263/) (2024)
- [Improved Techniques for Optimization-Based Jailbreaking on Large Language Models](https://mlsanity.com/paper/2405.21018/) (2024)
- [Cognitive Overload: Jailbreaking Large Language Models with Overloaded Logical Thinking](https://mlsanity.com/paper/2311.09827/) (2023)
- [CodeChameleon: Personalized Encryption Framework for Jailbreaking Large Language Models](https://mlsanity.com/paper/2402.16717/) (2024)
- [Beyond Single-Turn: A Survey on Multi-Turn Interactions with Large Language Models](https://mlsanity.com/paper/2504.04717/) (2025)
- [Against The Achilles' Heel: A Survey on Red Teaming for Generative Models](https://mlsanity.com/paper/2404.00629/) (2024)
- [AutoRedTeamer: Autonomous Red Teaming with Lifelong Attack Integration](https://mlsanity.com/paper/2503.15754/) (2025)
- [Conversational Contextual Bandit: Algorithm and Application](https://mlsanity.com/paper/1906.01219/) (2019)
- [A Survey on Contextual Multi-armed Bandits](https://mlsanity.com/paper/1508.03326/) (2015)
- [Enhancing Financial Report Question-Answering: A Retrieval-Augmented Generation System with Reranking Analysis](https://mlsanity.com/paper/2603.16877/) (2026)
- [Attack and defense techniques in large language models: A survey and new perspectives](https://mlsanity.com/paper/2505.00976/) (2025)
- [MAJIC: Markovian Adaptive Jailbreaking via Iterative Composition of Diverse Innovative Strategies](https://mlsanity.com/paper/2508.13048/) (2025)
- [Sustainable Hybrid Document-Routed Retrieval for Financial RAG: Resolving the Robustness-Precision Trade-off](https://mlsanity.com/paper/2603.26815/) (2026)
- [Adapting multi-armed bandits policies to contextual bandits scenarios](https://mlsanity.com/paper/1811.04383/) (2018)

## Built on by (most cited first, 1 of 1)

- [RedEvoAgent: Automatic Red-Teaming Agent with Experience-Driven Skill Evolution](https://mlsanity.com/paper/2608.27439/) (2026)

## Abstract (arXiv)

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.