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 violating response that the committee places on opposite sides of the boundary, differing by a handful of words where a model asked for both directly produces texts sharing almost nothing. A second constitution, for clinical triage, reproduces this on 18 obligations: 49 pairs at the same tightness, with the same modes hardest. Pairs like these show where an obligation's own terms stop deciding, which is what an agent deployed under it must be tested against, and the search finds them at a cost that scales with the boundary, not the text.

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