This study describes physical and mental health of incarcerated males aged ≥50 years who spent at least 20 consecutive years in prison, comparing those with life sentences ("lifers") with those expected to be released/paroled. Data included demographics, chronic medical conditions, self-reported and objective disabilities, depressive symptoms, suicidal ideation (SI), and social support. The 65 participants (Mage = 56.9, SD = 6.6) were racially diverse (40% White, 51% Black, 9% Hispanic/Other), incarcerated for M = 26.6 (SD = 4.5) years, and 34 (52%) were lifers. Among the 39 (60%) of participants with visitors, lifers had lower social support scores (p = .005). After controlling for age, race, and chronic conditions, lifers reported disability in a higher number of activities (p < .001), and had higher depressive symptoms (p = .08) and SI scores (p = .04). Health-related differences between lifers and those expected to be released have implications for prison systems including staff training, advance care planning, and need for expanding prison-based hospice programs.