© 2019, Yale Journal of Biology and Medicine Inc.. All rights reserved. Background: Clinicians at the bedside regularly encounter surprises or unexpected clinical developments that carry emotional, social, or moral overtones—especially when death is anticipated or when patients are particularly vulnerable. In such circumstances, clinicians may struggle to find practical clarity in making treatment plans that honor their fiduciary (literally, “entrusted”) duty to uphold equitably the ethical principles of beneficence, nonmaleficence, patient autonomy, and justice. Methods: We present the case of a patient who appeared to be actively dying and received an indwelling urinary catheter for the purpose of ensuring comfort. However, it led to an unintended reversal of renal failure and exacerbation of underlying psychiatric disease. This led to a meaningful change in the patient’s prognosis. It also created pragmatic challenges to shared decision making, which required an intentional interdisciplinary approach to balancing beneficence and patient autonomy. Conclusion: Palliative Care offers a holistic clinical approach to complex suffering. Palliative care specialists develop advanced skill sets in prognosis estimation, nuanced communication issues, and patient-centered goal setting. As this case highlights, prognosis can shift dramatically in the perimortem period, even with small changes in care plans. This case presented several biomedical, social-cultural, and ethical challenges to the team. Lessons from the case are presented regarding: the role a specialist palliative team might play throughout all stages of serious illness; approaching prognostication as an iterative rather than solitary task; and utilizing an ethical framework to care planning when there are barriers to shared decision making.