This chapter describes the design of a technology-supported learning environment in which small teams of students worked on authentic project tasks to develop a multimedia product for a real client. The students were enrolled in an advanced-level subject offered in a postgraduate education program, with most studying part-time, and many located a distance from the main campus. Jonassen’s (1999) model for a constructivist learning environment was used as the framework for the design of the subject. A key feature of this approach is the use of related cases to support authentic project activities. The specifics of the design were informed by the research and conceptual literature, and by pilot testing with two class groups. The implementation of the subject was the focus of a qualitative case study that investigated learners’ experiences of the environment. A rich set of data was collected, including student assignment work, discussion records and interviews. Analysis of the data provided insights into the role of the cases in supporting the collaborative project work.