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This article looks at existing and potential connections between two disparate subfields of historical inquiry: microhistory and Atlantic history. New research in the latter has utilized microlevel sources (those that allow the researcher to track an individual life) to challenge long-accepted generalizations about which kinds of people did what where in the eighteenth- and nineteenth-century Atlantic. But, the author suggests, such research raises specific methodological challenges and epistemological caveats. The risk is that we may borrow some of the more attractive elements of microhistory—in particular, the chance to tell extraordinary stories about ordinary lives—without addressing the elements of research design that give rigor and weight to the most persuasive microhistorical studies. Can microhistorical evidence from the Atlantic world serve as a basis for explanatory as well as descriptive claims? The article explores this question by discussing the author's own attempts to use microhistorical inquiry to answer macrolevel questions about the origins and breadth of anti-imperialism in the interwar British Caribbean.