Engagement, as a psychological concept, has been explored in numerous domains, including school and out-of-school time programs, and has been linked to positive developmental and achievement benefits in such domains. However, no research exists exploring engagement as it relates to the context of interscholastic athletics and the athletes who participate. Thus, this research sought to explore engagement through a qualitative investigation of 10 exceptional student-athletes. This study aimed to understand: (1) reasons why high-school athletes engage or do not engage in their interscholastic experiences; (2) what aspects of the environment contribute to high-school athlete engagement; and (3) what coaches can do to enhance engagement in their athletes. Results from in-depth interviews indicated that both environmental and individual factors contribute to engagement. Environmental factors included team and teammates, coaches, activities and drills, and other components of the environment (e.g., family, fan support). Individual factors included personal motivation for participation and personality. Lastly, coaches endeavoring to increase engagement in their athletes are recommended to show that they care about their athletes, understand and get to know their athletes better, and establish relationships with them off the field.