Studying perceived autonomy support, a basic tenet of self-determination theory (Deci & Ryan, 2000), provides some understanding as to how coaches can more positively influence youth athletes to enjoy and persist in youth sport. Borrowing insights from success in physical education and coaching-oriented interventions, the purpose of this paper was to highlight positive aspects and challenges of an innovative youth sport autonomy supportive training program for coaches. Positives included the initial training session and the use of an online training component. Challenges were the structure of the season, other coaches, and possibly the age of the athletes. Future training programs in youth sport coaching should increase in duration, provide specific examples of how to implement autonomy supportive coaching behaviors, as well as address solutions to the time constraints of the youth sport setting.