This chapter examines two key factors that influence the efficacy of online learning: student and teacher interaction and rapport. These two factors are heavily influenced by the stance that the learner takes. Online learning is opening up more possibilities for lifelong learning. This chapter will provide a critical discussion of online education, the theories that ground this delivery system, and the challenges that one university faculty had in creating a community of learners in a technology-mediated learning environment. “Let’s put our Reading Masters courses online,” the Dean suggested. “We need to move our graduate course offerings into the twenty-first century. Can’t be left behind.” She left the six of us in the conference room to talk over her proposal. But what was there to discuss? The answer was “No.” It just wasn’t possible. We’d lose that personal connection with our students that our university is known for. We’d lose those rousing discussions and meaningful interactions. Why, the students wouldn’t even see each other, let alone see us. How could we encourage lifelong learning when we weren’t even sold on the idea? The whole idea was impractical, unworkable, and inconceivable. Putting our courses online? Out of the question!