As the field of sport-for-development (SFD) has developed, there has been increasing debate over the ability of SFD programs to effect lasting structural change on target communities. Highlighting the barriers to SFD program delivery in five Pacific Island nations, in this paper we argue that numerous challenges emerging at macro-, meso-, and microlevels must be explored, understood, and accounted for to enact structural change. Building on thematic findings from our empirical cross-nation research project, we discuss the importance of addressing SFD challenges at all levels of society to ensure that interventions are appropriately tailored for the specific and often divergent sociocultural contexts in the Pacific Islands region. We argue for a more holistic approach to planning, management, and evaluation when attempting to deliver structural change through sport.