The increasing popularity of agile software development has significantly changed the way organizations plan, design, and implement software applications. However, considering the complexity involved with software development, the decision to choose an agile approach over the traditional waterfall approach is not straightforward. Organizations should carefully evaluate a variety of factors when choosing a development approach. In this teaching case study, the authors provide a discussion case to facilitate the students’ learning of using agile vs. traditional approaches in software development. This case study is developed based on experiences of multiple real-world software development projects and the literature on software development. It is designed to reflect the complexities students are likely to encounter in actual software development projects. The case can be used in undergraduate or graduate level management information systems courses that cover agile software development approaches. Students can gain an understanding of factors to consider when choosing a development approach, which tailors to the organization, the project environment, and the project team.