<p>This paper argues that abductive reasoning has a central place in theorizing Health Professions Education. At the root of abduction lies a fundamental debate: How do we connect practice, which is always singular and unique, with theory, which describes the world in terms of rules, generalizations, and universals? While abduction was initially seen as the ‘poor cousin’ of deduction and induction, ultimately it has something important to tell us about the role of imagination and humility in theorizing Health Professions Education. It is that which makes theory possible, because it allows us to ask what might be the case and calls attention to the role of creative leaps in theory. Becoming aware of the abductive reasoning we already perform in our research allows us to take the role of imagination—something rarely associated with theory—seriously.</p>