The number of aging and chronically ill prisoners continues to rise within the United Kingdom prison demography; consequentially, many institutions face health and social care crises of immense proportions. The needs of this group are both complex and costly, and in the United Kingdom, this is set to a backdrop of overcrowding, increasing violence, and public spending cuts in line with government austerity targets. In this context, the development of prisoner peer caregiving is proposed as an approach to mitigating the effects of aging, disability, and illness. A qualitative study was implemented to design, deliver, and evaluate a peer care training intervention within a UK prison. The perceptions of six prisoner peer caregivers are represented in this article. Thematic analysis of interview transcripts identified challenges experienced by peer caregivers in practice as well as practical solutions. The social processes underpinning prisoner peer caregiving are discussed, including individual and organizational impediments to the fulfillent of their role. Practice theory, social learning theory, and criminological sensitivities were used as theoretical lenses to analyze the findings.