Delivering bad news is an inevitable aspect of management. Teaching students to deliver bad news effectively and professionally can be successfully implemented into a course that addresses elements of managerial communication. In this article, we explain an experiential exercise that applies components of a three-phase model for delivering bad news. This exercise challenges students, working in groups, to plan and craft the text of an email message that delivers bad news and then to write a response to that message from the perspective of the participant. Students then analyze how other groups handled the same scenario. The exercise may fit with instruction about tone and word choice in written communication, especially as it relates to delivering bad news. The four-step exercise can be used in an undergraduate- or graduate-level course. Recommendations for adapting the exercise to the online environment are included.