In this paper, in the first place, I aim to enquire into Bernard Stiegler’s critical appropriation of his mentor Jacques Derrida’s notion of différance, emphasizing how Stiegler’s philosophy of technology stems from an original interpretation of the main tenets of deconstruction. From this perspective, I will investigate Stiegler’s definition of technology as tertiary retention, i.e., exosomatized, artificial memory interrelating with biological memory, testing its hermeneutic strengths as well as possible weaknesses. In the second place, I aim to contrast Stiegler’s understanding (...) of technology with the concept of multistability brought forward by postphenomenological philosophies of technology such as those elaborated by Don Ihde and Peter-Paul Verbeek. This investigation will enable me to submit that Stiegler’s approach represents a peculiar and innovative way to conceive of technology. On the one hand, indeed, it does not seem to fall prey to the criticisms raised by postphenomenology against traditional philosophies of technology such as Martin Heidegger’s or Jacques Ellul’s, deemed to be overly deterministic, abstract and pessimistic in their understanding of technology. On the other, it retains important methodological precautions from deconstruction, thereby pointing at some possible blind spots of postphenomenology, especially concerning the vexed question of the empirical-transcendental divide, which Stiegler aims to develop beyond both Derrida’s and postphenomenology’s stances. (shrink)