This qualitative case study investigates and analyzes the health and healthcare experience of elderly offenders. Four substantive areas which were examined included: 1) To explore how changes in an inmate's personal health and functional status influenced the healthcare process, 2) To explore how family relationship awareness and involvement affected prisoner health and healthcare, 3) To explore the influence of policy on prisoner health and healthcare and, 4) To explore the influence of the larger societal discourse on prisoner health and healthcare. The study was conducted within three theoretical frameworks: standpoint theory, Cantor's (2000) model of social care of the elderly, and the social construction of the aging inmate. Face-to-face and phone interviews were conducted with sixteen participants. Four of the participants were elder inmates between the ages of 50 and 90 years of age, and had served time in the state of Alabama's only correctional facility designed for the aged and infirm male prisoner. The additional twelve collateral participants were correctional staff, medical personnel, family members, and church and community volunteers. This research contributes to the literature on elderly offenders, and the understanding of experiencing health changes and healthcare in a correctional institution. The study concludes with several recommendations intended to better prepare prisons, healthcare providers and communities for the growing elderly inmate population.