Background: As people increasingly receive personal health information through technology, there is increased importance for this information to be communicated with empathy and consideration for the patient’s experience of consuming it. Although technology enables people to have more frequent and faster access to their health information, it could also cause unnecessary anxiety, distress, or confusion because of the sensitive and complex nature of the information and its potential to provide information that could be considered bad news. Objective: The aim of this study was to uncover insights for the design of health information technologies that potentially communicate bad news about health such as the result of a diagnosis, increased risk for a chronic or terminal disease, or overall declining health. Methods: On the basis of a review of established guidelines for clinicians on communicating bad news, we developed an interview guide and conducted interviews with patients, patients’ family members, and clinicians on their experience of delivering and receiving the diagnosis of a serious disease. We then analyzed the data using a thematic analysis to identify overall themes from a perspective of identifying ways to translate these strategies to technology design. Results: We describe qualitative results combining an analysis of the clinical guidelines for sharing bad health news with patients and interviews on clinicians’ specific strategies to communicate bad news and the emotional and informational support that patients and their family members seek. Specific strategies clinicians use included preparing for the patients’ visit, anticipating patients’ feelings, building a partnership of trust with patients, acknowledging patients’ physical and emotional discomfort, setting up a scene where patients can process the information, helping patients build resilience and giving hope, matching the level of information to the patients’ level of understanding, communicating face-to-face, if possible, and using nonverbal means. Patient and family member experiences included internal turmoil and emotional distress when receiving bad news and emotional and informational support that patients and family members seek. Conclusions: The results from this study identify specific strategies for health information technologies to better promote empathic communication when they communicate concerning health news. We distill the findings from our study into design hypotheses for ways technologies may be able to help people better cope with the possibility of receiving bad health news, including tailoring the delivery of information to the patients’ individual preferences, supporting interfaces for sharing patients’ context, mitigating emotional stress from self-monitoring data, and identifying clear, actionable steps patients can take next.