The empirical-transcendental debate in philosophy of technology, as debates go, took a turn toward the counterposing of the two perspectives, ‘empirical’-pragmatic-pragmatist versus ‘transcendental’-critical. Postphenomenology aligns itself with the former standpoint, and it is in this spirit that commentators have criticized it for its too-instrumentalist stance and lack of overarching, i.e., transcendental orientation. But the positions may have become too starkly delineated in order for the debate to reach any breakthrough: a seemingly unbridgeable gap yawns between the stances of ‘technology with (...) a small “t”’ and ‘Technology with a capital “T.”' Is there any way to reorient the debate? In this paper I propose to do so by considering whether there would be some way of arriving from one end of the spectrum to the other—crossing the gap. Exploring the purported wasteland in between “technology” and “Technology” by way of object-oriented ontology (OOO)—Harman, Morton—we can find it actually filled with countless gaps, adhering to every thing. Following the radical insights of OOO, we’d have to attest to a ‘thing-transcendentality.’ The ‘gap,’ then, that seemed so threatening and all-encompassing, becomes smeared out, levelled down to a multiplicity of perspectives. And this casts the debate, with its purported strict tension between ‘empirical’ and ‘transcendental’ positions, in fresh terms, opening up new ways for studying how the two interrelate. (shrink)