This chapter discusses the key points of communicating serious news to patients and their family members in the surgical settings. Surgeons deliver serious news in a variety of settings, such as the outpatient, inpatient, intensive care unit, and perioperative areas as well as the emergency trauma bay setting. Each setting presents some unique challenges and needs. We describe some of the best practices when delivering serious news to a patient in these situations. We also address the impact of these conversations on the surgeon, including coping with emotions and moral distress. Though effective communication skills are highly valued by surgeons, surgery training places less emphasis on building such skills as compared to teaching of procedural or technical skills. Therefore, some key knowledge, skills, and attitudes related to teaching effective communication skills to future surgeons are outlined.