When Prompt Optimization Becomes Jailbreaking: Adaptive Red-Teaming of Large Language Models

Safety-aligned large language models (LLMs) remain vulnerable to adversarial prompts that bypass their safety training. Existing automated red-teaming methods either require privileged access unavailable in production, rely on manually engineered per-model templates, or optimize a single objective without population-level diversity. We present REPRO (Reflective Evolutionary Prompt Optimization), a pure black-box framework that discovers adversarial prompts through evolutionary optimization driven entirely by a compressed open-weight 7B reflective model on a single consumer GPU. REPRO introduces two mechanisms absent from prior work, both isolated in a component ablation: semantic crossover, an LLM-guided multi-parent recombination operator, and Bayesian strategy selection via Thompson Sampling informed by structured failure analysis. We catalog REPRO's behavior on AdvBench, JailbreakBench, and HarmBench across 36 target models from 11 families, including GPT-5-nano, Claude-3.5-Sonnet, Gemini-2.5-Pro, and Grok-4.1. Under our protocol REPRO reaches 100% attack success rate (ASR) on every evaluated target in a single turn, at a median of 24 target queries per behavior. Two properties of the protocol qualify that figure. The judge scoring candidates during optimization also produces the reported ASR, and search halts when it accepts, so ASR reports whether search succeeded within the iteration budget rather than success at a fixed budget. All baseline figures are transcribed from their original papers, which use different judges, budgets, and model versions. We therefore present this as a catalog of model coverage under one protocol rather than a head-to-head ranking, and develop both qualifications in the paper.

Red-teaming is becoming a central part of large language model (LLM) safety evaluation, yet current practice still relies heavily on expert-written prompts or fixed benchmark suites. This creates a gap between what is easy to test and what deployed models can actually do: failures may be rare, context-sensitive, and distributed across many threat categories. We study automated red-teaming as a constrained adversarial search problem and introduce a learning-driven framework that couples category-aware attack generation with hierarchical vulnerability detection. The method starts from curated safety seeds, expands them through meta-prompt-guided and evolutionary search, and scores the resulting prompt--response pairs with lexical, semantic, and behavioral detectors. Across six threat categories on GPT-OSS-20B, the framework discovers 47 validated vulnerabilities, including 21 high-severity cases and 12 novel attack patterns. Under matched query budgets, it achieves a 3.9$\times$ higher discovery rate than manual expert red-teaming while maintaining 89% detection accuracy and full category coverage. Ablations show that the gains do not come from more prompts alone: diversity constraints prevent template collapse, coverage constraints prevent category blind spots, and semantic detection recovers failures missed by lexical rules. These results suggest that red-teaming can be made more scalable and reproducible when treated as adaptive search rather than as a static checklist.

Safety fine-tuning of language models typically requires a curated adversarial dataset. We take a different approach: score each candidate prompt's difficulty by how often the target model's own rollouts are judged harmful, then fine-tune on the hardest prompts paired with the model's own non-jailbroken rollouts. On Llama-3-8B-Instruct and Llama-3.2-3B-Instruct, this approach cuts the WildJailbreak attack success rate from 11.5% and 20.1% down to 1-3%, but pushes refusal on jailbreak-shaped benign prompts from 14-22% to 74-94%. Interleaving the same hard prompts 1:1 with adversarially-framed benign prompts (prompts that look like jailbreaks but have benign intent) cuts that refusal back down to 30-51% on 8B and 52-72% on 3B, at a cost of 2-6 percentage points of attack success rate. Within the mixed regime, training on the hardest half of the eligible pool rather than a random half cuts the remaining ASR by 35-50% (about 3 percentage points) on both models.