# X-Teaming Evolutionary M2S: Automated Discovery of Multi-turn to Single-turn Jailbreak Templates

arXiv: https://arxiv.org/abs/2509.08729 · HTML: https://mlsanity.com/paper/2509.08729/

## 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 17 of its 21 references that are in the map.
- First posted on arXiv 10 Sep 2025.

## Placed in

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

## Builds on (most cited first, 17 of 17)

- [Training language models to follow instructions with human feedback](https://mlsanity.com/paper/2203.02155/) (2022)
- [Training a Helpful and Harmless Assistant with Reinforcement Learning from Human Feedback](https://mlsanity.com/paper/2204.05862/) (2022)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Constitutional AI: Harmlessness from AI Feedback](https://mlsanity.com/paper/2212.08073/) (2022)
- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [Improving alignment of dialogue agents via targeted human judgements](https://mlsanity.com/paper/2209.14375/) (2022)
- [Humanity's Last Exam](https://mlsanity.com/paper/2501.14249/) (2025)
- [A StrongREJECT for Empty Jailbreaks](https://mlsanity.com/paper/2402.10260/) (2024)
- [Improving Alignment and Robustness with Circuit Breakers](https://mlsanity.com/paper/2406.04313/) (2024)
- [Pretraining Language Models with Human Preferences](https://mlsanity.com/paper/2302.08582/) (2023)
- [Scalable and Transferable Black-Box Jailbreaks for Language Models via Persona Modulation](https://mlsanity.com/paper/2311.03348/) (2023)
- [MasterKey: Automated Jailbreak Across Multiple Large Language Model Chatbots](https://mlsanity.com/paper/2307.08715/) (2023)
- [Removing RLHF Protections in GPT-4 via Fine-Tuning](https://mlsanity.com/paper/2311.05553/) (2023)
- [LLM Defenses Are Not Robust to Multi-Turn Human Jailbreaks Yet](https://mlsanity.com/paper/2408.15221/) (2024)
- [X-Teaming: Multi-Turn Jailbreaks and Defenses with Adaptive Multi-Agents](https://mlsanity.com/paper/2504.13203/) (2025)
- [M2S: Multi-turn to Single-turn jailbreak in Red Teaming for LLMs](https://mlsanity.com/paper/2503.04856/) (2025)
- [ObjexMT: Objective Extraction and Metacognitive Calibration for LLM-as-a-Judge under Multi-Turn Jailbreaks](https://mlsanity.com/paper/2508.16889/) (2025)

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

- [MacroBench: A Novel Testbed for Web Automation Scripts via Large Language Models](https://mlsanity.com/paper/2510.04363/) (2025)

## Abstract (arXiv)

Multi-turn-to-single-turn (M2S) compresses iterative red-teaming into one structured prompt, but prior work relied on a handful of manually written templates. We present X-Teaming Evolutionary M2S, an automated framework that discovers and optimizes M2S templates through language-model-guided evolution. The system pairs smart sampling from 12 sources with an LLM-as-judge inspired by StrongREJECT and records fully auditable logs. Maintaining selection pressure by setting the success threshold to θ = 0.70, we obtain five evolutionary generations, two new template families, and 44.8% overall success (103/230) on GPT-4.1. A balanced cross-model panel of 2,500 trials (judge fixed) shows that structural gains transfer but vary by target; two models score zero at the same threshold. We also find a positive coupling between prompt length and score, motivating length-aware judging. Our results demonstrate that structure-level search is a reproducible route to stronger single-turn probes and underscore the importance of threshold calibration and cross-model evaluation. Code, configurations, and artifacts are available at https://github.com/hyunjun1121/M2S-x-teaming.