The purpose of this study was to investigate how HIV-positive patients and infectious disease health care providers think about death, dying, and end-of-life care (EOLC) planning. We conducted separate in-depth qualitative interviews with 47 patients and 11 providers. Interview data were transcribed and analyzed using a secondary comparative method. Patients and providers demonstrated profound differences in their perspectives on patient empowerment and attributions of control related to disease progression, imminence of death, and EOLC decision making. Notably, patients described fears related to life-extending interventions that generally went unaddressed within the clinical context. We argue for the routinization of EOLC discussions and suggest novel research approaches to improve patient empowerment and medical engagement.