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.
Current approaches to LLM adversarial testing suffer from coverage gaps: manual red-teaming does not scale, LLM-as-attacker methods exhibit mode collapse, and gradient-based approaches produce uninterpretable gibberish. We introduce a quality-diversity evolutionary framework that operates at the semantic level, evolving interpretable attack strategies rather than token sequences. Using MAP-Elites, we maintain a diverse archive of attacks across behavioral dimensions (strategy type, encoding method, prompt length). In experiments across GPT-4o-mini, Claude 3.5 Sonnet, Gemini 2.0 Flash, and an open-weight coding model (Devstral-small-2), we discover distinct vulnerability profiles: GPT-4o-mini is vulnerable to hypothetical and multi-turn framing combined with ROT13 encoding (fitness 0.8), Gemini to direct attacks with ROT13 and multi-turn with Leetspeak (0.8), while Claude shows uniformly ambiguous responses across all strategies (max 0.4). The semantic representation produces interpretable attacks that reveal systematic, model-specific weaknesses, providing actionable insights for improving LLM safety and a reproducible baseline for evaluating future frontier models. Code and experiment artifacts are released at https://github.com/bassrehab/red-queen.
Safety evaluation of large language models (LLMs) relies largely on single-turn attack datasets and single-judge scoring, underestimating risk from adaptive multi-turn adversaries and reporting a single success rate that does not separate partially actionable outputs from those carrying complete operational detail. We propose AMT-X (Adaptive Multi-Turn Exploitation), a phase-structured multi-turn red-teaming framework. Unlike prior multi-turn attacks that rely on ad hoc escalation or free-form per-goal plans, AMT-X casts the attack as an explicit, reproducible multi-phase state machine driven by semantic signals from the victim, and replaces single-judge scoring with a multi-role jury whose phase-conditioned checklists gate success on actionable harm. Across six frontier victim models (queried under their default safety alignment, without added moderation layers) and seven Moderation sub-categories, AMT-X attains overall attack success rates of 97.6-100% under a lenient score threshold, but 66.7-78.6% under a stricter gate requiring complete, real, and operational detail: a gap of up to 33 percentage points between partially and fully actionable harm.
Red-teaming, or identifying prompts that elicit harmful responses, is a critical step in ensuring the safe and responsible deployment of large language models (LLMs). Developing effective protection against many modes of attack prompts requires discovering diverse attacks. Automated red-teaming typically uses reinforcement learning to fine-tune an attacker language model to generate prompts that elicit undesirable responses from a target LLM, as measured, for example, by an auxiliary toxicity classifier. We show that even with explicit regularization to favor novelty and diversity, existing approaches suffer from mode collapse or fail to generate effective attacks. As a flexible and probabilistically principled alternative, we propose to use GFlowNet fine-tuning, followed by a secondary smoothing phase, to train the attacker model to generate diverse and effective attack prompts. We find that the attacks generated by our method are effective against a wide range of target LLMs, both with and without safety tuning, and transfer well between target LLMs. Finally, we demonstrate that models safety-tuned using a dataset of red-teaming prompts generated by our method are robust to attacks from other RL-based red-teaming approaches.