As part of the general shift in contemporary healthcare from a focus on specific diseases to treating the whole person, doctors are now expected to be reflective and engage empathetically with patients. Yet, the context of end of life potentially confounds this commitment. Here we draw on the written submissions of UK medical students confronting dying patients to offer insight into a range of entangled issues. Although the exercise is designed to highlight the value of listening to patients and to encourage reflective practice, the experience of ultimately not being able to treat or cure frequently challenges the students’ understanding of the central purpose of clinical care and their future role as doctors. Because they invariably draw on the notion of ‘good death’, whenever they have to make sense of patient behaviour deemed as irrational or obstructive the students employ the concept of ‘denial’ as a strategic category. In this context denial is referred to as a disease-like object that the students feel they can, and should, diagnose and treat. Such conceptual operations consequently illustrate a tension arising from trying to acknowledge the value of a whole-patient approach while simultaneously reproducing the emphasis placed on identifying those discrete elements that determine legitimate medical intervention.