In this study, we used qualitative methods to help us better understand the experiences of instructors as they are persuaded to adopt a course management system and integrate it into their teaching. We discuss several patterns explaining how instructors implemented Blackboard, a CMS, by experimenting with individual features, facing both technical and integration challenges, and attempting to adapt Blackboard features to match their goals and practices. We also give explanations for why instructors either (a) embraced the tool and grew more dependent on it, (b) reduced their use of the tool to only some features, or (c) discontinued the tool and actively sought replacement options. In this paper we explain why instructors fell into any one of these three areas and what implications this may have for training and support needs.