Communicating bad news is never easy and for physicians these interactions may be a significant source of stress. To examine the characteristics that make delivering of bad news stressful, two studies were conducted. In the first study, 37 physicians generated 192 responses describing the characteristics that influence how difficult it is to break bad news. After sorting the responses in terms of common themes, six categories were identified: Physician, Patient, Institutional, Illness, Relationship, and Mishap. In Study 2, 115 physicians rated the degree of stress associated with each factor. Using principle component and reliability analyses, empirical support was found for six categories. A higher-order factor analysis suggested the existence of one over-arching factor. Items in the Mishap category were rated on average as the most stressful. Stress scores were largely unrelated to years in practice, experience delivering bad news or training.