In regulated industries like consumer finance, seemingly harmless user queries can exploit large language model vulnerabilities, triggering safety failures and pushing responses dangerously close to policy limits. Existing automated red-teaming methods trade off attack effectiveness against generation cost, while treating coverage, severity, and diversity as incidental rather than joint objectives. We introduce FinRT, a structured framework that builds reusable adversarial prompt generators from adaptive red-teaming strategies. Across the six victim models in consumer finance, FinRT substantially outperforms adaptive search baselines while amortizing target-facing attack generation into a reusable generator. FinRT nearly doubles the attack success rate over the adaptive baseline Rainbow Teaming (32.9% vs. 17.2%), increases maximum adversarial severity by 33%, and preserves comparable intra-policy-domain semantic diversity to iterative search methods. Our method achieves high cross-model transferability while exhibiting distinct victim-family specialization patterns.

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