Case studies have been found to improve student performance and help students develop problem-solving and decision making skills. The understanding of complexity of information technology, such as information security, relies on a curriculum with hands-on exercises. We used a unique hypothetical case study for a physician’s office in a health information security course. By working on the case study in teams, students linked the theoretical topics with practical experience, from strategic policy planning, tactical security planning, operational security planning, to audit standards. Students’ feedback shows their positive attitude toward the case study project. Students highly praised the project as exciting and challenging in that they have to act professionally in implementing a security system with a low failure rate. This paper reports our experience of using the case study exercises and discusses the potential improvement when using them again in the future.