Using historical and archival methodological approaches, this article provides an interdisciplinary empirical study of health experiences of prisoners in the Victorian convict prison in England and Wales. It explores the challenges of doing historical criminological work on prisoner health and disability. The article examines the health of long-term prisoners, those serving sentences of penal servitude and their interactions and treatment by the Prison Medical Officers in the system. Reflecting society outside, the prison population was drawn from populations that had experienced childhood illness, workplace accidents and war and therefore had to accommodate those suffering from both short- and long-term health issues. Using historical documentation and case studies of individual prisoners, this article highlights not only the deep scepticism the system had for those they saw as ‘malingerers’, but also the recognition that some people could not endure the full force of the prison labour regime.