# EvoFlint: An Evolutionary Atlas of Multi-Turn LLM Vulnerabilities

arXiv: https://arxiv.org/abs/2609.00487 · HTML: https://mlsanity.com/paper/2609.00487/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Prompt injection and agent security, one of 12 directions in LLM safety and security.
- Builds on 11 of its 24 references that are in the map.
- First posted on arXiv 31 Aug 2026.

## Placed in

- LLM safety and security / [Prompt injection and agent security](https://mlsanity.com/safety/prompt-injection-and-agent-security/)

## Builds on (most cited first, 11 of 11)

- [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)
- [Refusal in Language Models Is Mediated by a Single Direction](https://mlsanity.com/paper/2406.11717/) (2024)
- [Promptbreeder: Self-Referential Self-Improvement Via Prompt Evolution](https://mlsanity.com/paper/2309.16797/) (2023)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [MART: Improving LLM Safety with Multi-round Automatic Red-Teaming](https://mlsanity.com/paper/2311.07689/) (2023)
- [X-Teaming: Multi-Turn Jailbreaks and Defenses with Adaptive Multi-Agents](https://mlsanity.com/paper/2504.13203/) (2025)
- [Speak Out of Turn: Safety Vulnerability of Large Language Models in Multi-turn Dialogue](https://mlsanity.com/paper/2402.17262/) (2024)
- [Multi-Turn Context Jailbreak Attack on Large Language Models From First Principles](https://mlsanity.com/paper/2408.04686/) (2024)
- [FERRET: Framework for Expansion Reliant Red Teaming](https://mlsanity.com/paper/2603.10010/) (2026)

## Abstract (arXiv)

Frontier language models that refuse harmful single-turn prompts often comply when the same intent is reached gradually over many turns, making multi-turn attacks one of the least understood failure modes of large language models. Most automated red-teaming methods treat this as a generation problem: produce attacks that break the model. We argue it is better framed as a search problem: discover, organize, and iteratively refine a diverse archive of attack strategies, producing a structured map of how a target model fails rather than a list of one-off successes. We introduce EvoFlint, which applies evolutionary quality-diversity search to multi-turn red-teaming. Attack strategies are phased conversation plans, not raw prompts, and are evolved through LLM-driven mutation and crossover. A Pareto fitness over attack success rate and peak severity preserves selection signal from near-miss attacks. A risk-indexed archive runs novelty search with local competition over strategy description embeddings inside each cell, maintaining diversity without committing to a predefined style taxonomy. A generation-level memory accumulates target-model insights across the population and feeds them back into strategy generation. On the HarmBench-test split, EvoFlint reaches attack success rates of 35.8% on Claude Sonnet 4.6, 59.7% on GPT-5.4, and 94.3% on Qwen3-32B, alongside 98.7% on the older GPT-4o included as a baseline reference. The resulting archive, organized by risk category, exposes for each target which categories of harm its safety training has and has not covered.