Penumbra: Sample-Efficient Adversarial Search for Regulatory Obligations

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.

Financial institutions operate under dense, frequently amended rulebooks, and answering a compliance question correctly requires not only fluency but verifiable grounding in the authoritative text. Large language models are attractive for this task, yet the models that firms can realistically deploy on-premise are compact ones, and compact models hallucinate obligations. We study whether a carefully domain-adapted retrieval-augmented generation pipeline closes that gap. Our retriever is built in three stages on top of LegalBERT: entailment tuning that recasts question--passage matching as premise--hypothesis reconstruction, contrastive tuning with in-batch negatives, and score-level fusion with BM25. Our generator is a compact model (2B--12B parameters) served under 4-bit quantization, either prompted or adapted with retrieval-aware fine-tuning (RAFT) through LoRA. On ObliQA, a question-answering benchmark built from the Abu Dhabi Global Market rulebooks, the staged retriever raises Recall@10 from 0.256 to 0.774 and outperforms BM25 (0.678) and E5-large-v2 (0.758), the strongest general-purpose dense encoder we tested. RAFT-LoRA then improves the composite RePASs answer-quality score for every model we could adapt, with the largest gain on the weakest one. However, the adapted models do not transfer to Australian case-law questions, and a closed-book model that receives no passages at all scores within 0.011 RePASs of the full pipeline while producing answers that cite nothing and misstate obligations. The retrieval gain is therefore measured directly, the generation gain is a gain in RePASs rather than demonstrated grounding, and grounding itself requires an evaluation protocol that RePASs does not provide.

LLM agents in financial markets may cite rules yet still submit orders that violate executable constraints or misread surveillance evidence. We introduce ReguSim, a controlled financial-compliance environment, and ReguBench, a target-marked monitoring benchmark, to separate four artifacts: stated reasoning, attempted action, execution enforcement, and monitor evidence. In trader runs with DeepSeek V4 Pro and Gemini 3.5 Flash, visible rules reduce but do not eliminate rejected actions, and incentive or persona framing shifts behavior. A bridge study shows that trader rationales can mislead an independent monitor unless enforcement evidence is shown. In monitoring, simple structured baselines either match or exceed prompt-only LLMs. The results frame financial compliance evaluation as an audit of rule-grounded actions and evidence use, rather than a single compliance score.