Cross-Generational Transfer of Adversarial Attacks Reveals Non-Monotonic Safety Alignment in LLMs

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.

LLM-based agents process external content, exposing them to prompt injection and multi-turn manipulation. Most safety benchmarks evaluate defenders against fixed attack pools collected before evaluation, single-turn or multi-turn. We present a 21-scenario benchmark for \emph{adaptive multi-round attacks against memoryless LLM defenders}: an autonomous LLM attacker observes prior defender responses and pivots across rounds, while each defender response is evaluated as a fresh interaction. Holding the 21 scenarios, attackers, defenders, and structured-output scoring fixed, restricting scoring to the first attacker turn yields $0$-$1\%$ attack success rate (ASR); allowing 15 rounds of adaptive attack yields $5.4$-$14.0\%$. Pooling three frontier attacker LLMs uncovers $1.4$-$2.2\times$ as many unique successful attacks as the best single attacker, and the generated attacks have low cosine similarity ($0.02$-$0.14$) to attacks in existing benchmarks. Claude Opus 4.6 and GPT-5.4 are tied in aggregate ($5.4\%$ each; overlapping $95\%$ CIs), but their weaknesses differ sharply: on one scenario Opus reaches $60\%$ ASR ($95\%$ CI $36$--$80\%$) while GPT-5.4 and Gemini each stay at $7\%$ (CI $1$-$30\%$; the gap is preserved in a higher-$N$ replication). $13$ of $21$ scenarios distinguish at least one defender pair, yet rankings disagree across scenarios (Kendall's $W = 0.19$). We release the benchmark -- 21 evaluation scenarios, 10 public development scenarios, the orchestrator, baseline harnesses, and a multi-attacker CLI -- plus 945 transcripts from the 3$\times$3 frontier matrix, an attack-replay dataset, and 18{,}422 gpt-oss-20b battles from an open competition's final scoring rounds.

Large language models remain vulnerable to adversarial prompts that elicit harmful outputs. Existing safety paradigms typically couple red-teaming and post-training in a closed, policy-centric loop, causing attack discovery to suffer from rapid saturation and limiting the exposure of novel failure modes, while leaving defenses inefficient, rigid, and difficult to transfer across victim models. To this end, we propose EvoSafety, an LLM safety framework built around persistent, inspectable, and reusable external structures. For red teaming, EvoSafety equips the attack policy with an adversarial skill library, enabling continued vulnerability probing through simple library expansion after saturation, while supporting the evolution of adversarial vectors. For defense learning, EvoSafety replaces model-specific safety fine-tuning with a lightweight auxiliary defense model augmented with memory retrieval. This enables efficient, transferable, and model-agnostic safety improvements, while allowing robustness to be enhanced solely through memory updates. With a single training procedure, the defense policy can operate in both Steer and Guard modes: the former activates the victim model's intrinsic defense mechanisms, while the latter directly filters harmful inputs. Extensive experiments demonstrate the superiority of EvoSafety: in Guard mode, it achieves a 99.61% defense success rate, outperforming Qwen3Guard-8B by 14.13% with only 37.5% of its parameters, while preserving reasoning performance on benign queries. Warning: This paper contains potentially harmful text.