This case study explores how a community-based truancy prevention program mediates against absenteeism, truancy, and dropping out and positively transforms the lives of Black and Latina/Latino middle school youth. Findings suggest that community-school partnerships are critical in the quest to combat truancy and the alarming dropout rate among urban youth. This study also shows how committed individuals can work to engage and empower low-income urban youth who are disengaged from school. Extensive interviews and observations with Latina/Latino and Black youth demonstrate how the intervention program mediates against social and academic failure. Using grounded theory, this article explores four student-identified dimensions that impact his/her (re)engagement with school: (a) the importance of space that promotes peer relations, (b) incentive structures within programs, (c) the need for social networks, and (d) youth advocacy as a mechanism for institutional accountability. Implications for combating truancy, reducing dropout, and promoting student engagement are discussed. (Contains 2 figures.)