What will philosophy of technology be as its practitioners depart from the crossroads of the ideas of Don Ihde and Bernard Stiegler? Their two lines of thought confront and cross each other, giving rise to different ways of understanding technologies. Rather than following one or the other of these directions, I propose an Erörterung of such crossroads. As Martin Heidegger’s 1953 commentary on Georg Trakl’s poetry (Die Sprach im Gedichte) insists, Erörterung means, first, “to point out the proper place or site of something to situate it (das Weisen in den Ort),” and, second, “to heed that place or site (das Beachten des Ortes).” This Erörterung has to be conducted at multiple times, on multiple levels, as each of them hermeneutically identifies its own site. I proceed first through an Erörterung of the crossroads of the thinking of technology after Ihde and Stiegler, and second through an Erörterung of the Ort or the site of the first Erörterung, where the Ort for Heidegger is the land of the evening, the Occident [Abendland], in the throes of globalization, or more precisely Americanisation, a form of disorientation, that obscures the unconcealment of the essence of the human-technology relationship central to Heidegger. In the third part, I propose that the way to integrate and extend Heidegger, Ihde, and Stiegler is to acknowledge the importance of historical, cultural, and geopolitical difference in the interrelationship between the cosmos, morality, and technical activities, what I call cosmotechnics.