This research sought to describe the physical and psychological health and quality of life among older adult men incarcerated in a state prison and to examine the role of age and historical time between age cohorts. Survey responses from male respondents incarcerated in a medium-security prison (N = 186) were described using frequencies and descriptive statistics; chi-square and analysis of variance analyses were used to examine differences between age cohorts. The average number of chronic health conditions for the sample was higher than those in similar samples; the proportion of older adults with four or more chronic conditions was 10% higher than the national average for adults age 65 or older. Depression and post-traumatic stress (PTS) symptom severity scores were higher than those found in community-based samples. Significant differences were identified between cohorts regarding physical (number of chronic conditions, F = 12.48, p < .01); functional impairment, F = 4.28, p < .05) and psychological health (PTS symptom severity, F = 3.16, p < .05). Policy and practice implications are discussed including the expansion of on- and off-site services for older adults in prisons, enhanced accessibility, and the use of grief counseling and stress management strategies.