A training module of six sessions was designed for professors in higher education who were transitioning to teaching synchronous, e-learning courses from formerly teaching in either asynchronous courses or in face-to-face courses. Since the participants were experienced educators, the boundary of their expertise to be extended was moving to the fully synchronous e-learning setting. All of the professors were already familiar with their institution's asynchronous learning management system and some were familiar with asynchronous courses with synchronous elements. This research follows the professors through the transition to fully synchronous classes, documenting the challenges and lessons learned in this journey through observations of the training, individual interviews and one focus group. One year after teaching their first synchronous, e-learning course(s), their reflections on the training provide some insights into the kinds of changes the professors experienced as they extended the boundaries of their teaching and learning environments and entered new territory. One finding of the study is that more explicit discussion of theoretical underpinnings of e-learning, such as technology abilities, affordances and constraints, and transformative-pedagogies, might have helped the professors navigate this transition more easily.