This study examined the efficacy of an afternoon and weekend academic program called the "Community School Initiative" (CSI) during the COVID-19 pandemic. CSI was offered to racialized students and families from the Jane and Finch community in Toronto which is one of the most under-resourced neighbourhoods in Canada. It involved a partnership between private social enterprise "Spirit of Math" and non-profit organization "Youth Association for Academics, Athletics, and Character Education" (YAAACE). Seven teachers participated in a focus group and 33 students and parents completed a survey to express their experiences attending the CSI. Findings were identified using thematic analysis from a Critical Race Theory paradigm. Key characteristics of effective structural community-programming were identified. The results highlight the importance of access to opportunities in a culturally reflective manner to ensure student success through continuity of care particularly on evenings and weekends involving a team of caring educators.