Sandy Chan’s chapter explores how patients and families present to the healthcare system with their own histories and cultures, many of them challenged and underserved. Once they enter the healthcare culture, they are burdened by having to communicate with a system that regularly engages in systematic oppression where there are significant power dynamics that need to be navigated. The healthcare culture often drains the psychosocial and spiritual resources of the patient and family. Chan presents clinical vignettes from her work as a frontline palliative care social worker that illustrate these issues. She discusses and analyzes them through the lens of her experience as a clinical social worker and her current role as the operational director of the palliative care department. She also discusses the concept of “palliative care as reparations,” whereby patients and families can experience high level transdisciplinary care from a palliative care team that help foster healing and repair in their healthcare journey.