This paper explores inmates and prison health care workers perceptions of the state of health care services in four correctional facilities in South Africa. Structural and organisational issues are explored in terms of how they impact the delivery and provision of health care to inmates within correctional facilities. Additionally, the study forms an access point analysis of prisons as a health care setting as part of the development and testing of a STI/HIV health education intervention for soon to be released inmates. Focus group discussions (6-8 participants per group) were conducted with male inmates in four facilities in KwaZulu-Natal and Mpumalanga provinces. Individual face-to-face interviews were conducted with eight health personnel to get a view from both providers and end users of health care in correctional settings. Data were analysed thematically. We found strong evidence of prison being a strategic point to increase access to health services for offenders. Curative services within prisons were well established and running despite the presence of certain challenges varying across institutions. Prevention programmes emerged as an area that requires stronger emphasis to facilitate imparting skills and promoting safer practices for inmates upon release. Peer-led education programmes emerged as a key aspect of preparation for release and community reintegration amongst inmates.