Recapitulating two recent trends in Heidegger-scholarship, this paper argues that the transcendental theme in Heidegger’s thought clarifies and relates the two basic questions of his philosophical itinerary. The preparatory question, which belongs to Being and Time , I.1–2, draws from the transcendental tradition to target the condition for the possibility of our openness to things: How must we be to access entities? The preliminary answer is that we are essentially opened up ecstatically and horizonally by timeliness. The fundamental question, which belongs to the unpublished Being and Time , I.3, and the rest of Heidegger’s path of thinking, is accessed by means of the first. In a turn of perspective, it targets that in terms of which we relate to the givenness of being. Heidegger first attempts to handle this question using the transcendental language of temporal horizon before happening upon the terminologically more fitting “event of appropriation” and thereafter criticizing transcendental terms. By reconstructing the preparatory question and its reversal, we can see that Heidegger’s later criticism of transcendence in fact relies on its initial success. The turn from timeliness to appropriation (initially by means of transcendental temporality) happens within the domain initially disclosed by the preparatory question.