The problem of providing mandated medical care has become commonplace as correctional systems in the United States struggle to manage unprecedented increases in its aging prison population. This study explores older incarcerated women's perceptions of prison health care policies and their day-to-day survival experiences. Aggregate data obtained from a sample of 327 older women (mean age = 56) residing in prison facilities in five Southern states were used to identify a baseline of health conditions and needs for this vulnerable group. With an average of 4.2 chronic health conditions, frequently histories of victimization, and high rates of mental health issues, the women's experiences of negotiating health care was particularly challenging. By incorporating the voices of older women, we expose the contradictions, dilemmas, and obstacles they experience in their attempts to obtain health care. It is clear from the personal accounts shared that, despite court mandates, penal harm practices such as delaying or denying medical treatment as well as occasional staff indifferences are common in women's prisons. With older women having the greatest need for health care, an age- and gender-sensitive approach is recommended.