Across Canada and around the world, online technologies are becoming widely used and accepted as effective modes of learning. This essay traces the initial forays into teaching online classes by three Faculty of Education professors at one small Canadian university and an instructional designer/teacher who joined part-way through the research journey. Included are our understandings of how our teaching practices evolved amidst initial uncertainties and expanding abilities, our renewed awareness of the importance of collegial support and encouragement, and the implications for future online teaching experiences. Our essay provides an intimate window into our online teaching journeys and captures specific moments we experienced at various stages in the development of our e-instructional practices. The account of our processes of becoming online teacher educators is supported by an interweaving of historical and current literature on pedagogy and e-learning, and serves to address the dearth of research into the processes educators undergo when engaged in online teaching.