Many community-based sport and physical activity programs take a positive youth development approach when operating in underserved communities around the world (Forneris, Whitley, & Barker, 2013). However, one of the biggest challenges for these programs is sustainability (Lindsey, 2008). The purpose of this article is to present the 3 authors' experiences related to program sustainability when working with community-based sport and physical activity programs using a positive youth development approach in underserved communities. The authors describe the challenges faced with program sustainability, including ineffective development approaches, building strong relationships with community partners, knowledge translation, and securing funding. Also described are the strategies used to overcome these challenges, such as planning, capacity building, recruitment, and evaluation. This article is intended to stimulate more open and honest discussions about the realities of positive youth development program sustainability around the world.