For individuals with an intellectual disability, emerging adulthood (18–25 years) may be a disruptive time with an abrupt ending to programming and services after adolescence. This study critically explores the social environment and experiences of individuals involved in a Special Olympics paddling program for emerging adult athletes with an intellectual disability. Using an instrumental case study design, multiple qualitative methods were implemented including photography, videography, observations, and interviews. The participants included four athletes (one female and three male; three with autism spectrum disorder, one with mild intellectual disability), three fathers, a coach, a program coordinator, and an administrator. Analyses were guided by interpretivism and the quality parasport participation framework. The findings highlight how the limited staff training and preparation, the complexity of providing such a program, and parental hidden labor in their adult children’s sport involvement influence the social environment. Implications for coaching practices include the importance of communication strategies and coach education.