In the wake of an international crackdown against preferential tax regimes, Caribbean tax havens and other jurisdictions have adopted “due diligence” procedures to manage financial and reputational risk. Due diligence relies on qualitative forms of evaluation and defers grounded and definitive knowledge claims through continuous peer review. In doing so, it mirrors certain forms of ethnographic practice at a number of levels of scale. This article tracks the shifts in financial regulation from crime to harm and from certainty to scrutiny and reflects on their implications for ethnography—as a limited and open-ended process of evaluation warranted by qualitative forms of judgment. It seeks to complicate our picture of contemporary capitalisms by drawing attention to the nonquantifiable and the ethical that lie “inside” them. Where conventional forms of ethnographic critique might look to expose the political or economic interests behind actions, symbols, or social relationships, this article has a more modest goal: to try to understand the similarity of form between due diligence and anthropology.