With an increasing number of terminal patients in the United States dying in the context of hospice, the role that hospice chaplains play in providing spiritual care for patients and their families is important to examine. The hospice chaplain role requires careful navigation of the development of relationships that may end abruptly, the expectations of hospice organizations, and the needs of both patients and families. The current study uses the concept of competing role dialectics to further our understanding of the challenges chaplains face as they enact this crucial role. Data from 45 current and former hospice chaplains reveal four major role tensions hospice chaplains must develop strategies to handle: fostering relationships versus fostering autonomy, acting as team members versus acting as individuals, serving the family unit as a whole versus serving particular family members, and following the agendas of patients and families versus following one’s own agenda.