The out-of-school time (OST) field in the United States has a complex history. The push to offer programming reflects a legacy rooted in moral panics about racially minoritized youth. However, this field is populated by community spaces that act as multipurpose sites of culturally sustaining educational practices supporting positive youth development. We report findings from interviews with OST leaders, youth workers, policy influencers, and youth about how to create, sustain, and protect more liberatory and humanizing practices, demonstrating that racism and deficit-based thinking continue to inform programmatic practices and youth experiences. Furthermore, this study reveals that programs with expansive ideas of youth voice, healing justice, and whole-child approaches to youth development create better opportunities for connection and belonging.