This paper is an analysis of the issues encountered in the process of building a community of practice amongst students through engaging in online dialogue using WebCT. The analysis is guided by an educational change framework, proposed by Goodell, Parker, and Kahle (2005), which includes Technical, Political, Cultural, Moral, and Personal dimensions. First, the analysis highlights the reasons for using WebCT. Second, the issues faced in using WebCT effectively are discussed. Finally, suggestions are offered for instructors using WebCT for the first time.