This book explores and formulates a response to the question: How best can those held in modern systems of mass incarceration be cared for pastorally when many prisons diminish both hope and humanity? Employing the multi-disciplinary approach of practical theology, this ethnographic enquiry will be a guide for chaplains and all who strive to embody compassion wherever human flourishing is undermined. The book’s structure follows the pastoral cycle method from practical theology, remaining context-based and practice-focused throughout. Pastoral insights are illustrated with personal, poetic and movingly reflective material drawn from the lived experience of indeterminately sentenced men who did not know if or when they would be ever released. The author, a former prison chaplain, remains reflexively and humanely present in the text, modelling the profound humane regard and pastoral presence that is central to this work. This book will take the reader deeply into penal spaces on a journey of both compassion and hope.