This article presents the first stage of a design-based research project to introduce case-based learning using existing interactive technologies in a major Australian university. The paper initially outlines the relationship between case-based learning, student interaction and the study of interactions--and includes a review of research into technologies supporting varying types of interaction. We then introduce design-based research (DBR) as a way of improving student interaction within an undergraduate e-business course while simultaneously adding practical and theoretical insights to the literature in the field. Applying DBR, we present the learning environment used and analyse the interactions observed. The paper concludes with a summary of our findings concerning instructional means to make online interactions more meaningful and a discussion of future research activities within the project using design-based research.