In this article, we discuss how the Harvard Method of case study, Interactive Communication Technologies, and Cognitive Flexibility Theory may contribute to case-based learning about business decision-making. In particular, we are interested in designing learning environments that foster critical thinking, creativity, and reasoning that entertains multiple hypotheses from multiple perspectives. We posit a framework for implementation and evaluation based upon Jonassen, Peck, and Wilson's "Meaningful Learning" model and Iowa's "Integrated Thinking Model." Based upon this framework, we describe the design and features of Panteon, a Web-based system for diagnosing complex business cases. We report the results of an evaluation of Panteon, utilizing focus group interviews, observations, and questionnaires to investigate participants' assessment of Panteon in comparison to the Harvard Case approach. Results indicate that both students and business experts favored Panteon for its affordances to stimulate higher order cognitive skills. The implications and limitations of the evaluation are discussed.