The chapter examines global risks that are exceedingly complex and characterized by the long time horizons entailed in their governance. It argues that the dynamics of climate change, biodiversity loss, pandemics, and other system-spanning challenges are now forcing pragmatists and skeptics alike to push their thinking beyond the kinds of experiments in risk governance discussed in previous chapters. They suggest the need for profound socioeconomic transformation, eventually forcing deep structural political change at the system level. Complex and slow-moving crises with transnational dimensions will not be managed successfully by nation-states assigning priority to their own autonomy. The essential question comes back to the fore. Might the “insuring instinct” today be harnessed in zones that stretch the limits of risk calculation quickly enough to sustain more ambitious forms of collaborative governance? More specifically, can existing political authorities in vital and inherently complex policy arenas effectively deploy insurance narratives to move beyond voluntary and reversible intergovernmental arrangements without provoking self-defeating backlashes? The chapter reviews current analyses of key cases where private insurance reach their limits, but insurance metaphors promise to be politically useful.