This book gives an account of the nature and content of compassion and its role in healthcare. The argument considers how and why contested beliefs about political life, suffering, the human condition, time, and responsibility make a difference to ‘compassion’. While compassion appears to be a straightforward aspect of life and practice, the appearance is deceptive. Compassion is plagued by both conceptual and practical ills and needs some quite specific kinds of therapy. The first step therefore is to diagnose precisely what is wrong with ‘compassion’ including its debilitating political entanglements, the vagueness of its meaning and the risk of burn-out it threatens. With diagnosis in hand, three therapies are prescribed for compassion’s ills: (i) an understanding of patients and healthcare workers as those who pass through the life-course, encountering each other as wayfarers and pilgrims; (ii) a grasp of the nature of compassion in healthcare; and (iii) an embedding of healthcare within the realities of civic life. With this therapy applied, the argument shows how compassionate relationships acquire their content in healthcare practice. First, the form that compassion takes is shown to depend on how different doctrines of time, tragedy, salvation, responsibility, fault, and theodicy set the terms of people’s lives and relationships. Second, how such compassion matters to practice and policy is worked out in the detail of healthcare professionalism, marketisation, and technology, drawing on the author’s collaborations. Covering everything from conception to old age, and from machine learning to religious diversity, this book draws on philosophy, theology, and everyday experience to stretch the imagination of what compassion might mean in healthcare practice.