In this article, I blend a review of existing research, results from an original qualitative study, and a decade of personal experience in order to examine the facilitation of significant learning experiences in asynchronous online courses. Research has repeatedly demonstrated that students who enroll in online courses do so for reasons of convenience, and not because they feel they learn best in this environment. Self-determination theory research in online learning, which examines psychological need support and satisfaction in the online context, has yielded inconsistent findings. In light of this research, I interviewed online students about their motivation for taking online courses and their experiences doing so. Students reported significant learning experiences, which were subsequently analyzed using the method of descriptive phenomenology. The analysis revealed that, in order for significant learning to occur, students must perceive the course material to be personally relevant, and they must perceive that their instructor is available for dynamic interactions. I carefully describe these features and provide personal examples of how to achieve these necessary conditions in online courses.