This chapter considers three areas of healthcare practice and policy, selected because of collaborative work that has been pursued by the author and in light of the challenges they pose to compassion. For the first, healthcare professionalism, it draws on work with the Royal College of Physicians London to consider how the doctor’s roles as healer, patient-partner, advocate, and innovator, matter for compassionate relationships in practice, addressing especially the challenge of machine learning. The second concerns marketisation in healthcare, including both its corrosive and beneficial effects on compassionate relationships. The role of faithfulness and covenant in healthcare practice is explored, resulting in a recommendation for a Healthcare Covenant binding together public, healthcare professionals, researchers, and corporate actors. The third, drawing on partnership with biomedical researchers and clinicians, concerns the technologisation of healthcare, specifically in the field of precision medicine. The discussion examines problems with the culture of precision medicine and practical ideas to strengthen compassionate relationships.