Prisoners’ hopes for a life without suffering—without causing and experiencing harm—are embedded in practices of ethical becoming and ideas of transcendence. These hopes are somehow both more banal and complex than the literature on hope generally suggests; they emerge because of lack and are signs of despair, rather than realistic prospects or opportunities. Based on longitudinal interview data ( N = 452) with short-term prisoners in Norway and England & Wales, this article shows how hope functions as an orientation through different phases of a prison sentence as well as post-release regardless of whether it materializes. With inspiration from Lear’s idea of ‘radical hope’, I describe prisoners’ hopes as a mode of living with more emphasis on where hope comes from rather than what it leads to, thus following recent prompts to distinguish between hopes derived from opportunities from deeper hopes grounded in despair. I outline prisoners’ pain upon entry into custody and show how their ‘ground projects’—the things without which they would not care to go on with their lives—become clear when they are taken away. In this conceptualization, short-term prisoners’ hopes are in many ways a manifestation of despair fused with ethical deliberations on what kind of person one wishes to become and to whom one owes something.