In the Introduction to the Critique of Judgment, Kant equates the a priori principle of judgments of taste with that of the “formal purposiveness of nature.” Yet a logical gap persists between the principle for constructing a system of empirical laws and the principle of taste, the latter concerning merely the form of an object’s intuition: the former pertains to “relations of laws,” whereas the latter concerns “the form of the object.” This gap can be bridged only by re-examining the “technical” and “heautonomous” character of the power of judgment in the First Introduction, and by establishing these concepts as the common foundation of both the logical and aesthetic employments of that faculty. Doing so not only establishes the legitimacy of the power of judgment as the bridge between nature and freedom, but also reveals that—through a transcendental “technique” that analogizes nature to art—this faculty encompasses logical, aesthetic, and real purposiveness. This perspective also illuminates an important shift in Kant’s conception of the Critique of Judgment: from the “judgment of taste,” grounded in the universal communicability of human feeling, to the “critique of the power of judgment” as the mediating faculty between nature and freedom.