This article investigates the relationship between moral judgments, fallibility, and imaginative insight. It will draw heavily from the canon of classical American philosophy, the members of which (from Ralph Waldo Emerson, to C.S. Peirce, E.L. Cabot, to Jane Addams, to John Dewey) took up this relationship as pivotally important in moral theorizing. It argues that the process of hypothesis formation—characterized as “insight” by Emerson and extended by Peirce in his notion of “abduction”—is a necessary condition of moral progress for it (...) allows individuals to think through the boundaries of social and ethical life. In a world of unexpected occurrences and uncertainty, the ability to generate novel explanatory frameworks and normative ideals is a crucial, if normally underappreciated, moral faculty. This paper attempts to respond to this relative neglect. (shrink)