This chapter argues that mountain biking can serve to both mitigate the trauma associated with ‘Nature’s’ destruction, whilst helping to imagine a range of ‘post-natural’ futures. Drawing on the recently translated works of Bernard Stiegler, it contends that the negentropic qualities of mountain bike culture comprises a performative response that enables practitioners to encounter, witness and reorient to the contemporary current climate crisis. In particular, it proffers that it is the very uncanniness of the mountain bike as a technological artifact that renders an experience that is both constitutive of and distanciated from, the surfaces, materials and environments with which it interacts. Mountain bikes and mountain bike trail building tools, are positioned as ‘therapeutic prescriptions’ that facilitate practices of care and attention within a specific social system, whilst assuaging the nihilistic discourse of existing Anthropocene thinking. These careful practices, which include getting ‘dirty’, and the active enrolment of non-human labour, as well as the collective conversations and contestations that stem from these, are argued to facilitate more deliberative relationships with the environment, whilst engendering new and emerging forms of (onto)political subjectivity that are made to the measure of the (Neg)Anthropocene.