In America’s prisons, long‐term incarceration carries fears that one could die in prison alone and abandoned. Death by incarceration looms as inescapable for myriad inmates who are terminally ill or “graying” in prison. These realities inform this study of a prison‐based hospice program staffed by male inmate volunteers in a mixed medium/maximum security facility. Of special concern are the experiences of the men who sit by the bedside of others who are dying. I begin with the assumption that prisons loom as states of exception, epitomized by the realities of substandard prison medicine, the devaluation of care as anathema to prison survival, and the persistent neglect of the ill and aging. The ethos and practices associated with inmate‐driven end‐of‐life care demarcate an inverted space of non‐judgmental praxis that simultaneously envelopes the dying man while also instigating self‐reflection, change, and self‐care among inmate hospice volunteers.