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I explicate and defend Kant's analysis of “skepticism” as a single, metaphilosophically unified rational phenomenon (at A756–764/B784–797, for instance). Kant anticipates one of the defining trends of contemporary epistemology's approach to radical philosophical skepticism: the thought that skepticism cannot be directly refuted, by demonstrating its falsity, but must be diagnosed, to show that its premises are unnatural, and consequently fail to be rationally compelling from within our own nonskeptical standpoint. Kant's most ambitious claim here is that he will develop this diagnosis in a unitary fashion, by demonstrating that Cartesian, Humean, Pyrrhonian, and Agrippan skepticism are essentially interrelated as so many means to “the skeptic's” defining philosophical end. This “unity thesis” comes in both weak and strong variations. First, and more weakly, Kant argues that apparently distinct skeptical problematics share certain crucial metaphilosophical assumptions about the nature of reason, and the role of philosophical self-knowledge. More strongly, he also claims that the four problematics just mentioned are related hierarchically, in that the more fundamental skeptical worries constitute the essential dialectical context for the less fundamental ones, such that the more superficial problematics only arise if a logically prior worry is first acceded to. By showing how deeply these two unity theses structure Kant's Critical methodology, I argue that the Kantian view of philosophy as a “doctrine of wisdom” incorporates, and arguably surpasses, a number of key insights found in more recent work. The final result is that the transcendental philosopher may hope to co-opt the attractions of skepticism without making any unnecessary concessions along the way.