Until the start of the COVID-19 pandemic, the remand population in England and Wales had remained relatively stable. Following the shuttering of courtrooms across England and Wales, the remand population began to increase, marking a departure from the historically stable trends amongst this prison sub-population. The increase has taken up space in the public discourse, being remarked upon by media, parliamentarians, and non-governmental organizations. However, in spite of recent attention, remand has been an under-researched topic. In comparison with other forms of incapacitation (e.g., terms of imprisonment), experiences of remand custody remain largely under-explored and under-conceptualized. This thesis fills this gap by empirically exploring the experiences of 20 adult men with a history of being detained before their trial and/or sentencing date. Given the realities of conducting research in a pandemic, which precluded entry into custodial environments, participants in this study were adult men with previous experience of being either unconvicted or unsentenced prisoners. Interviews revealed three dominant pains associated with periods of time detained on remand: the pains of disruption, the pains of disempowerment, and the pains of uncertainty and liminality. The findings of this study depict the challenges associated with being confined before trial and/or sentencing, both interior to the prison and outside it, and lend weight to existing notions that criminal justice institutions have punitive tendencies. By identifying the pains associated with confinement in pre-trial and pre-sentence detention, this research explores approaches which would allow the pains of remand to be incorporated in the measurement of penal severity and into punishment proper.