This set of caselets includes three health insurance scenarios designed for an in-class exercise within a session focusing on the health insurance industry and health care. These scenarios provide perspectives from the three major stakeholders involved in health care: the employer who is paying, the families who are receiving the care, and the providers who are giving the care. Students consider challenges unique to each of these stakeholders and make decisions. This exercise usually lasts 30–45 minutes and could follow a didactic lecture on health insurance or could kick off a class on health insurance to open the students’ eyes to the issues in this industry. At the Darden School of Business, this is taught in the second-year course "Challenges in Healthcare: A Systems Overview"; it would also be suitable in a module covering innovations in health care.