Given the documented benefits associated with organized sport and thus the assumption that youth who leave sport are losing out on developmental benefits, dropout has been predominantly framed as a crisis to be solved. Throughout this paper we aimed to challenge the overarching narrative of youth dropout from organized sport as a negative outcome only by highlighting the complexity of youth sport experiences and participation patterns. First, we highlight the lack of conceptual clarity regarding the term “dropout” and question its relevance for describing youth’s sport experiences. Next, we discuss how declines in organized sport participation may reflect developmentally appropriate transitions in sport and broader physical activity for youth and across the life span. Finally, we suggest that, at times, disengagement may be a positive and protective outcome for youth when the sport environment is harmful. Recommendations for future research and practice are provided to advance the understanding of youth sport experiences and participation patterns.