Prison health is an emerging, interdisciplinary area of research, which can be both challenging and rewarding in equal measure. This article seeks to articulate the methodological, practical, and ethical challenges in conducting qualitative prison health research involving some 22 prison governors and officers across 17 prison establishments in England. In investigating the impact of macroeconomic austerity on prison health, the article details the process of participant recruitment and data collection over a 14-week period. It then critically evaluates the research practicalities concerning the three-stage institutional ethical approval process, involving the Ministry of Justice, the academic institution, and each prison establishment, as well as how responses from these prison actors can be solicited given that the topic is regarded as politically sensitive. This article concludes by considering how prison health researchers should embrace fieldwork challenges by being adaptable, resilient, and self-reflective. While these processes are situated in prison health research, lessons and their significance can be refined and adopted to other areas of research while also being sensitive to the idiosyncrasies of the research settings and disciplines.