# The Art of the Jailbreak: Formulating Jailbreak Attacks for LLM Security Beyond Binary Scoring

arXiv: https://arxiv.org/abs/2605.09225 · HTML: https://mlsanity.com/paper/2605.09225/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Safety alignment and jailbreak attacks, one of 10 directions in LLM alignment / RLHF / preference optimisation.
- Builds on 18 of its 29 references that are in the map.
- First posted on arXiv 9 May 2026.

## Placed in

- LLM alignment / RLHF / preference optimisation / [Safety alignment and jailbreak attacks](https://mlsanity.com/alignment/safety-alignment-and-jailbreak-attacks/)
- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Builds on (most cited first, 18 of 18)

- [Gemma 3 Technical Report](https://mlsanity.com/paper/2503.19786/) (2025)
- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [WildGuard: Open One-Stop Moderation Tools for Safety Risks, Jailbreaks, and Refusals of LLMs](https://mlsanity.com/paper/2406.18495/) (2024)
- [Jailbreaking Leading Safety-Aligned LLMs with Simple Adaptive Attacks](https://mlsanity.com/paper/2404.02151/) (2024)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [JailBreakV: A Benchmark for Assessing the Robustness of MultiModal Large Language Models against Jailbreak Attacks](https://mlsanity.com/paper/2404.03027/) (2024)
- [AmpleGCG: Learning a Universal and Transferable Generative Model of Adversarial Suffixes for Jailbreaking Both Open and Closed LLMs](https://mlsanity.com/paper/2404.07921/) (2024)
- [Robust Prompt Optimization for Defending Language Models Against Jailbreaking Attacks](https://mlsanity.com/paper/2401.17263/) (2024)
- [An LLM can Fool Itself: A Prompt-Based Adversarial Attack](https://mlsanity.com/paper/2310.13345/) (2023)
- [SelfDefend: LLMs Can Defend Themselves against Jailbreaking in a Practical Manner](https://mlsanity.com/paper/2406.05498/) (2024)
- [Bag of Tricks: Benchmarking of Jailbreak Attacks on LLMs](https://mlsanity.com/paper/2406.09324/) (2024)
- [When LLM Meets DRL: Advancing Jailbreaking Efficiency via DRL-guided Search](https://mlsanity.com/paper/2406.08705/) (2024)
- [JAILJUDGE: A Comprehensive Jailbreak Judge Benchmark with Multi-Agent Enhanced Explanation Evaluation Framework](https://mlsanity.com/paper/2410.12855/) (2024)
- [h4rm3l: A language for Composable Jailbreak Attack Synthesis](https://mlsanity.com/paper/2408.04811/) (2024)
- [PAPILLON: Efficient and Stealthy Fuzz Testing-Powered Jailbreaks for LLMs](https://mlsanity.com/paper/2409.14866/) (2024)
- [TwinBreak: Jailbreaking LLM Security Alignments based on Twin Prompts](https://mlsanity.com/paper/2506.07596/) (2025)
- [Improved Generation of Adversarial Examples Against Safety-aligned LLMs](https://mlsanity.com/paper/2405.20778/) (2024)
- [One Model Transfer to All: On Robust Jailbreak Prompts Generation against LLMs](https://mlsanity.com/paper/2505.17598/) (2025)

## Abstract (arXiv)

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.