# A Representation Engineering Perspective on the Effectiveness of Multi-Turn Jailbreaks

arXiv: https://arxiv.org/abs/2507.02956 · HTML: https://mlsanity.com/paper/2507.02956/

## Key facts

- Cited by 10 papers in the map (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 18 of its 23 references that are in the map.
- First posted on arXiv 29 Jun 2025.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)
- Mechanistic interpretability / [Steering and probing for LLM safety](https://mlsanity.com/mechinterp/steering-and-probing-for-llm-safety/)

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

- [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)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [Representation Engineering: A Top-Down Approach to AI Transparency](https://mlsanity.com/paper/2310.01405/) (2023)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [Improving Alignment and Robustness with Circuit Breakers](https://mlsanity.com/paper/2406.04313/) (2024)
- [Deliberative Alignment: Reasoning Enables Safer Language Models](https://mlsanity.com/paper/2412.16339/) (2024)
- [Constitutional Classifiers: Defending against Universal Jailbreaks across Thousands of Hours of Red Teaming](https://mlsanity.com/paper/2501.18837/) (2025)
- [COLD-Attack: Jailbreaking LLMs with Stealthiness and Controllability](https://mlsanity.com/paper/2402.08679/) (2024)
- [LLM Defenses Are Not Robust to Multi-Turn Human Jailbreaks Yet](https://mlsanity.com/paper/2408.15221/) (2024)
- [Soft Prompt Threats: Attacking Safety Alignment and Unlearning in Open-Source LLMs through the Embedding Space](https://mlsanity.com/paper/2402.09063/) (2024)
- [Automated Red Teaming with GOAT: the Generative Offensive Agent Tester](https://mlsanity.com/paper/2410.01606/) (2024)
- [Taxonomy, Opportunities, and Challenges of Representation Engineering for Large Language Models](https://mlsanity.com/paper/2502.19649/) (2025)
- [X-Boundary: Establishing Exact Safety Boundary to Shield LLMs from Multi-Turn Jailbreaks without Compromising Usability](https://mlsanity.com/paper/2502.09990/) (2025)
- [Steering Dialogue Dynamics for Robustness against Multi-turn Jailbreaking Attacks](https://mlsanity.com/paper/2503.00187/) (2025)
- [Tempest: Autonomous Multi-Turn Jailbreaking of Large Language Models with Tree Search](https://mlsanity.com/paper/2503.10619/) (2025)
- [Well, that escalated quickly: The Single-Turn Crescendo Attack (STCA)](https://mlsanity.com/paper/2409.03131/) (2024)

## Built on by (most cited first, 10 of 10)

- [State-Dependent Safety Failures in Multi-Turn Language Model Interaction](https://mlsanity.com/paper/2603.15684/) (2026)
- [Furina: Fragmented Uncertainty-Driven Refusal Instability Attack](https://mlsanity.com/paper/2605.26158/) (2026)
- [BinaryShield: Cross-Service Threat Intelligence in LLM Services using Privacy-Preserving Fingerprints](https://mlsanity.com/paper/2509.05608/) (2025)
- [The Salami Slicing Threat: Exploiting Cumulative Risks in LLM Systems](https://mlsanity.com/paper/2604.11309/) (2026)
- [D-Judge: Disrupting Multi-Turn Jailbreaks using Semantics-Preserving Output Rewriting](https://mlsanity.com/paper/2606.02640/) (2026)
- [On the Inseparability of Instructions and Data in Shared-Embedding Sequence Models](https://mlsanity.com/paper/2606.27567/) (2026)
- [Mitigating Many-shot Jailbreak Attacks with One Single Demonstration](https://mlsanity.com/paper/2605.08277/) (2026)
- [From AI-Generated Content to Agentic Action: Security and Safety Threats in Generative AI](https://mlsanity.com/paper/2605.16471/) (2026)
- [Evaluating Language Model Safety Across Long Adversarial Conversations](https://mlsanity.com/paper/2609.38357/) (2026)
- [The Geometry of Harmfulness in Multi-Turn Attacks](https://mlsanity.com/paper/2609.38389/) (2026)

## Abstract (arXiv)

Recent research has demonstrated that state-of-the-art LLMs and defenses remain susceptible to multi-turn jailbreak attacks. These attacks require only closed-box model access and are often easy to perform manually, posing a significant threat to the safe and secure deployment of LLM-based systems. We study the effectiveness of the Crescendo multi-turn jailbreak at the level of intermediate model representations and find that safety-aligned LMs often represent Crescendo responses as more benign than harmful, especially as the number of conversation turns increases. Our analysis indicates that at each turn, Crescendo prompts tend to keep model outputs in a "benign" region of representation space, effectively tricking the model into fulfilling harmful requests. Further, our results help explain why single-turn jailbreak defenses like circuit breakers are generally ineffective against multi-turn attacks, motivating the development of mitigations that address this generalization gap.