Canadian jails are increasingly being used to hold pre-trial rather than sentenced prisoners. In fact, a growing number of individuals are serving a significant portion of their sentence by way of banked remand credit (Deshman and Myers 2014). This temporal reconfiguration has important implications for the very nature of 'punishment,' yet studies of jail experiences remain scarce within penal scholarship (Irwin 1985; Welch 1999; Walker 2014; Griffin 2006). This dissertation explores the experiences of men and women who spent time as a pre-trial and/or sentenced prisoner at the Ottawa-Carleton Detention Centre (OCDC), a notorious jail located in Canada's capital city. Employing Sexton's 'subjective' conceptualization of punishment, and drawing on interviews conducted with 33 participants, I consider how prisoners define, perceive and respond to conditions at OCDC. Prisoners' accounts reveal that much of what is experienced as 'punishment' in the jail context relates to unintended yet profound forms of physical and symbolic harm (Sexton 2015). Central to prisoners' accounts were the pains of 'warehouse' living, guard-prisoner dynamics, medical mistreatment and health damage. The emphasis on such pains illustrates not only the salience of 'unintended' harms (Sexton 2015), but the extent to which the body remains implicated in the experience of punishment. Interestingly, these pains were not necessarily ameliorated by the social world produced by prisoners, as Sykes (1958) observed in his classic study. Instead, the institutional dynamics of the jail gave way to a culture marked by tension, mistrust and violence, while also impairing the ability of individuals to imbue the carceral experience with counter-punitive meaning. Prisoners' resistant efforts both in and outside of the jail walls, however, point the dialectical nature of power, or the ways in which objects of power can react in ways that undermine its purported objectives (Foucault 1977).