Case-based learning has long been used to bring students into contact with the complexity of real-world situations. Despite this popularity and considerable history, research into how case analysis can support future problem-solving has been limited. The study reported in this paper investigated learners’ understanding of multimedia instructional design and development derived from the analysis of two richly detailed cases, and how this understanding then supported learners in their own design projects. A qualitative case study approach was used to follow a class of Masters students engaged in a technology- supported, case-based learning environment. Student work from case analysis, group project and reflective tasks was the key data source, complemented by interviews with students and their instructor, observations of class meetings, and the collection of online discussion list records and electronic resource files. The study found that the case analysis task raised learners’ awareness of design approaches and project management strategies, and that discussion and reflection play critical roles in developing students’ understanding. The study also highlighted some limitations of the case approach, suggesting the need for strategies that support learners’ thinking and reasoning.