Adsensory technology presupposes a neoliberal entrepreneurial self as an integral feature of its biopolitical financialisation of healthcare regimes. According to Michel Foucault, neoliberalism is indebted to the endeavour of its self-disciplined subjects, investing human capital in a self-regulated, entrepreneurial pursuit of responsible healthcare and well-being. Primarily informed by social network analytics and virtual ethnographic observations, this book identifies the biopolitical basis of adsensory technologies. It argues that a paradoxical feature of adsensory technologies dissimulating “that there is nothing” (Jean Baudrillard) is the proliferation of risk. This is because the dissimulation of nothing opens up the possibility that “everything can be a risk, in so far as the type of event it falls under can be treated according to the principles of insurance technology” (Francois Ewald). Adsensory wearable technologies are called upon as “a strategy of deterrence” (Jean Baudrillard) to indemnify capitalism’s production of signs which dissimulate their simulation. In a context in which much that was certain now feigns its own existence, the insurance professed by adsensory technologies provides for an unrealisable guarantee against indefinable unknowable risks. Based also on case studies of European Court of Justice personal finance insurance rulings, this book engages critically with the neoliberal construct of the entrepreneurial lifestyle insurance subject. Social network analytics are utilised here to map bio-technology onto neoliberal regimes of financialised well-being and healthcare provision. In so doing, the book situates adsensory technologies within the marketising healthcare management programmes that are currently aligning the neoliberal reengineering of health and well-being citizenship with the biopolitical healthcare financialisation of populations. Paradoxically, in their endeavour to actor network virtual well-being health communities, adsensory technologies proliferate the individuating marketised conditions of neoliberal self-regulating entrepreneurialism. This gives rise to aleatory materialist dialectics of financialised surveillance far exceeding the regulatory time and space modalities of Foucauldian panoptics and Mathiesen synoptics. Adsensory technologies are integral to a seismic transformation in the cultural economies of time presently eliding digital advertising and insurantial technologies. Axiomatic with the synchronic times of the adsensory technologies valorised by lifestyle insurance, much riskier asynchronic embodied times, transgressively dissimilating the limits of financialisation, are beginning to emerge.