Patients with cancer face multiple stresses near death. Diverse symptoms, contemplating mortality and accuracy of prognostication, loss of functioning, changing family dynamics, financial strain, and frequent interactions with the health care system are the norm (Committee on Approaching Death: Addressing Key End of Life Issues; Institute of Medicine 2015). Many patients experience emotional difficulty even in the absence of mental health comorbidities. Oncologists who treat patients near death often experience emotional difficulty themselves, including sadness, anticipatory grief, shock, anger, and regret. They face the prospect of having frequent emotionally draining conversations, often with patients they have known for a long time. This commentary explores an important area of clinical practice introduced by the target article" The Inner Lives of Doctors: Physician Emotion in the Care of the Seriously Ill"(Childers and Arnold 2019): the unique challenges in caring for patients at this stage in the face of prognostic uncertainty. We present an overview of the role of prognostic uncertainty in oncologists' emotions, why the landscape of prognostication for cancer