In the multi-faceted domain of adult online education, administrators, researchers, and practitioners have an opportunity to assist adults who bring unique experiences, talents, challenges, and needs to the online learning environment. The purpose of this chapter is to refresh the reader's awareness about two theories: student involvement and transactional distance. It is the hope of the author that a heightened understanding of these theories will spark new ideas, research, and practices, facilitating successful outcomes. Taken individually or paired as theoretical or conceptual frameworks, these theories are seminal to both adult and distance education domains. Researchers, decision-makers, and practitioners are encouraged to objectively observe their educational environments through the lenses of these two theoretical perspectives and consider what is working and what is not working in the context of today's rapidly changing cultural, socio-political climate.