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This article explores the bases of Kant’s cosmopolitanism in his more systematic writings on freedom, judgment, and community. My argument is that, if we peer beneath his more explicitly normative prescriptions for achieving “perpetual peace,” we find the tools not just of a cosmopolitan vision but what we might call a “cosmopolitical method.” While many assume Kant’s political thought descends directly from his moral philosophy, a look back at relevant passages in the first Critique reveals an alternative reading that points toward his theory of reflective judgment, which combines practical freedom with judgments based on theoretical concepts. Of particular importance is Kant’s conception of community as commercium, through which Kant discerns all matters of right to concern the way free actors are constrained to share the earth in common. These considerations allow for a broader way of thinking about Kantian cosmopolitanism, one that is responsive to the reflective judgment of world citizens as they encounter new challenges.