Penumbra: Sample-Efficient Adversarial Search for Regulatory Obligations

Anthony Rhodes

Agents are entering finance, healthcare and law, sectors where a violation leaves no lexical signature and carries real penalties. Whether an omission is material, or a disclosure sufficient, depends on what the response left out. Probing such an obligation means finding responses one minimal edit from flipping compliance, and every probe costs a generation and two adjudications, so the binding constraint on regulatory red-teaming is sample efficiency, not volume. We introduce Penumbra, an adversarial search that walks from a verified anchor under an expanding edit budget until a two-evaluator committee changes its verdict, and emits the two adjacent responses that straddle the change. Allocation is adaptive, and the objective is coverage of the defeat surface: distinct (obligation x defeat mode) cells resolved per candidate. At matched budget, adaptive allocation reaches uniform allocation's full-budget coverage on 59% of the candidates; at equal records it covers 1.43x the defeat modes of naive enumeration, and the gain is confined to the axis it targets. On 60 screened obligations of a financial advisory constitution, Penumbra returns 144 pairs, each a compliant and a…