# AutoAdv: Automated Adversarial Prompting for Multi-Turn Jailbreaking of Large Language Models

arXiv: https://arxiv.org/abs/2511.02376 · HTML: https://mlsanity.com/paper/2511.02376/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 16 of its 65 references that are in the map.
- First posted on arXiv 4 Nov 2025.

## Placed in

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

## Builds on (most cited first, 16 of 16)

- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (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)
- [Red Teaming Language Models with Language Models](https://mlsanity.com/paper/2202.03286/) (2022)
- [Universal Adversarial Triggers for Attacking and Analyzing NLP](https://mlsanity.com/paper/1908.07125/) (2019)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [Rainbow Teaming: Open-Ended Generation of Diverse Adversarial Prompts](https://mlsanity.com/paper/2402.16822/) (2024)
- [AutoDAN-Turbo: A Lifelong Agent for Strategy Self-Exploration to Jailbreak LLMs](https://mlsanity.com/paper/2410.05295/) (2024)
- [AdvPrompter: Fast Adaptive Adversarial Prompting for LLMs](https://mlsanity.com/paper/2404.16873/) (2024)
- [LLM Defenses Are Not Robust to Multi-Turn Human Jailbreaks Yet](https://mlsanity.com/paper/2408.15221/) (2024)
- [ImgTrojan: Jailbreaking Vision-Language Models with ONE Image](https://mlsanity.com/paper/2403.02910/) (2024)
- [Automated Red Teaming with GOAT: the Generative Offensive Agent Tester](https://mlsanity.com/paper/2410.01606/) (2024)
- [Leveraging the Context through Multi-Round Interactions for Jailbreaking Attacks](https://mlsanity.com/paper/2402.09177/) (2024)
- [Jailbreaking and Mitigation of Vulnerabilities in Large Language Models](https://mlsanity.com/paper/2410.15236/) (2024)
- [Tempest: Autonomous Multi-Turn Jailbreaking of Large Language Models with Tree Search](https://mlsanity.com/paper/2503.10619/) (2025)
- [Human-Interpretable Adversarial Prompt Attack on Large Language Models with Situational Context](https://mlsanity.com/paper/2407.14644/) (2024)

## Abstract (arXiv)

Large Language Models (LLMs) remain vulnerable to jailbreaking attacks where adversarial prompts elicit harmful outputs. Yet most evaluations focus on single-turn interactions while real-world attacks unfold through adaptive multi-turn conversations. We present AutoAdv, a training-free framework for automated multi-turn jailbreaking that achieves an attack success rate of up to 95% on Llama-3.1-8B within six turns, a 24% improvement over single-turn baselines. AutoAdv uniquely combines three adaptive mechanisms: a pattern manager that learns from successful attacks to enhance future prompts, a temperature manager that dynamically adjusts sampling parameters based on failure modes, and a two-phase rewriting strategy that disguises harmful requests and then iteratively refines them. Extensive evaluation across commercial and open-source models (Llama-3.1-8B, GPT-4o mini, Qwen3-235B, Mistral-7B) reveals persistent vulnerabilities in current safety mechanisms, with multi-turn attacks consistently outperforming single-turn approaches. These findings demonstrate that alignment strategies optimized for single-turn interactions fail to maintain robustness across extended conversations, highlighting an urgent need for multi-turn-aware defenses.