A high-level review of existing literature on E-Commerce (EC) education reveals the need for a more theory-driven approach to further research on the development of EC education. In response to this need, the problem of EC education is analysed in this paper from a contextualist perspective found in the literature on organizational change and strategy. Specifically, Pettigrew’s contextualist framework of research and analysis is adopted here to analyse the problem of EC education and its development. In the paper, we provide a brief expose′ of this framework in terms of its major premises and conceptual constructs. This is followed by a systematic application of the contextualist approach to analyse the current scenario of EC education in terms of its broader context, its content, as well as the change processes involved. Our analysis facilitates a logical identification of the key issues and challenges involved in EC education and its future development. A discussion of selected issues and challenges is presented along with some recommendations.