While scholars have paid considerable attention to Heidegger’s creative reinterpretation of Kant’s transcendental philosophy, little interest has been given to tracing the methodological steps by which the former’s work can house the key epistemic themes of the latter (e.g., those raised in the Critique of Pure Reason) within a broader, ontological problematic. To rectify this shortcoming, I propose outlining a “Diltheyan loop,” in order to make explicit a tapestry of presuppositions by which Heidegger anchors the epistemic themes of theoretical knowing (e.g., the possibility of synthetic a priori judgments) in the pre-theoretical, pre-predicative, and pre-discursive level of self-understanding (in which the possibility of understanding being [Sein] is also rooted). By showing how this “Diltheyan loop” is operative in the fore-structure of Heidegger’s Kant-interpretation, I will illuminate the overall strategy by which he recasts, retrieves, and reinterprets the key motifs of the Critique of Pure Reason, which at the same time will shed light on the controversies and criticisms that have arisen in the subsequent decades.