# Evaluating Language Model Safety Across Long Adversarial Conversations

arXiv: https://arxiv.org/abs/2609.38357 · HTML: https://mlsanity.com/paper/2609.38357/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Safety alignment, refusal and guardrails, one of 12 directions in LLM safety and security.
- Builds on 35 of its 47 references that are in the map.
- First posted on arXiv 29 Sep 2026.

## Placed in

- LLM safety and security / [Safety alignment, refusal and guardrails](https://mlsanity.com/safety/safety-alignment-refusal-and-guardrails/)

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

- [Lost in the Middle: How Language Models Use Long Contexts](https://mlsanity.com/paper/2307.03172/) (2023)
- [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)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [Llama Guard: LLM-based Input-Output Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2312.06674/) (2023)
- [Towards Understanding Sycophancy in Language Models](https://mlsanity.com/paper/2310.13548/) (2023)
- [Red Teaming Language Models with Language Models](https://mlsanity.com/paper/2202.03286/) (2022)
- [BeaverTails: Towards Improved Safety Alignment of LLM via a Human-Preference Dataset](https://mlsanity.com/paper/2307.04657/) (2023)
- [Discovering Language Model Behaviors with Model-Written Evaluations](https://mlsanity.com/paper/2212.09251/) (2022)
- [AutoDAN: Generating Stealthy Jailbreak Prompts on Aligned Large Language Models](https://mlsanity.com/paper/2310.04451/) (2023)
- [Open Problems and Fundamental Limitations of Reinforcement Learning from Human Feedback](https://mlsanity.com/paper/2307.15217/) (2023)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [Capabilities of GPT-4 on Medical Challenge Problems](https://mlsanity.com/paper/2303.13375/) (2023)
- [GPTFUZZER: Red Teaming Large Language Models with Auto-Generated Jailbreak Prompts](https://mlsanity.com/paper/2309.10253/) (2023)
- [JailbreakBench: An Open Robustness Benchmark for Jailbreaking Large Language Models](https://mlsanity.com/paper/2404.01318/) (2024)
- [Safety Alignment Should Be Made More Than Just a Few Tokens Deep](https://mlsanity.com/paper/2406.05946/) (2024)
- [LLMs Get Lost In Multi-Turn Conversation](https://mlsanity.com/paper/2505.06120/) (2025)
- [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 Holistic Approach to Undesired Content Detection in the Real World](https://mlsanity.com/paper/2208.03274/) (2022)
- [Improving Alignment and Robustness with Circuit Breakers](https://mlsanity.com/paper/2406.04313/) (2024)
- [ShieldGemma: Generative AI Content Moderation Based on Gemma](https://mlsanity.com/paper/2407.21772/) (2024)
- [ToxicChat: Unveiling Hidden Challenges of Toxicity Detection in Real-World User-AI Conversation](https://mlsanity.com/paper/2310.17389/) (2023)
- [SALAD-Bench: A Hierarchical and Comprehensive Safety Benchmark for Large Language Models](https://mlsanity.com/paper/2402.05044/) (2024)
- [Scalable and Transferable Black-Box Jailbreaks for Language Models via Persona Modulation](https://mlsanity.com/paper/2311.03348/) (2023)
- [Do-Not-Answer: A Dataset for Evaluating Safeguards in LLMs](https://mlsanity.com/paper/2308.13387/) (2023)
- [X-Teaming: Multi-Turn Jailbreaks and Defenses with Adaptive Multi-Agents](https://mlsanity.com/paper/2504.13203/) (2025)
- [SimpleSafetyTests: a Test Suite for Identifying Critical Safety Risks in Large Language Models](https://mlsanity.com/paper/2311.08370/) (2023)
- [Inadequacies of Large Language Model Benchmarks in the Era of Generative Artificial Intelligence](https://mlsanity.com/paper/2402.09880/) (2024)

## Abstract (arXiv)

Conversational safety evaluations often test language models with a single harmful prompt, even though real-world systems interact with users through long, adaptive conversations. This study examines whether models continue to respond safely when an adversarial user persists across multiple turns. We evaluate three open-weight, instruction-tuned models on two harmful prompts across different conversation lengths and random seeds. In each setting, a second language model acts as a persistent adversarial user, while a safety classifier labels every response as safe or unsafe. Across all model-prompt combinations, first-turn safe-response rates ranged from 85% to 100%. By depth 11, they dropped to 38-61%, and by depth 101, to 15-44%. This decline appeared across models and continued well beyond the short interactions typically used in multi-turn safety evaluations. These results provide proof-of-concept evidence that strong single-turn safety does not necessarily persist during sustained adversarial interaction. They highlight the need for long-horizon evaluations and conversation-level safeguards that account for risk accumulating across turns.