This chapter presents three fictitious case studies of organizations facing decisions to convert one or several courses to distance learning. As you read through the cases, you will be presented with the issues that many real organizations face when trying to decide whether, and to what extent distance learning should be implemented in their organization. Two of the cases presented depict commercial organizations, and the third represents an higher education institution. Each case presents background information on the organization, major stakeholders, and the current state of distance learning initiatives within the organization. Each case focuses on a different aspect of the analysis for distance learning. The first case covers the strategic analysis, the second presents a course conversion analysis, and the third presents an infrastructure analysis. Together, these should walk the reader through several analysis issues faced in real world situations.