This dissertation examines the experiences of the Roses in Concrete Community School (RiC) in East Oakland, California. Conceived as a counter-hegemonic schooling project, RiC responded to the community’s demand for self-determination in education; the school’s founders sought to fulfill this demand by designing a school organized around a culturally sustaining/revitalizing and healing-centered program dedicated to serving predominantly Black and Latinx children and families of Oakland. This project centers on a central research question: How does a school that was deliberately designed to counter the adverse conditions in a low-income urban community meet the social-emotional and academic needs of the students and communities it serves? I conceptualize the theoretical framework of Frontier Education, or white settler colonial schooling practices, and schooling as marronage, or liberatory schooling practices grounded in autonomous community and freedom, to guide this analysis. Decolonizing, critical Indigenous, and critical race methodologies also guide the data collection strategy used in this research. Using a critical ethnographic case study approach, I analyzed observations, documents, and interviews with key stakeholders from the school’s design stage in 2014 until its fifth year of operation in 2020. Three key findings emerged from this case study. First, RiC successfully adopted a community responsive approach to student and family engagement, prioritized an alternative model of student success embodied by the concept of the Warrior Scholar, utilized an Ethnic Studies-based, Spanish-English dual immersion, arts-oriented social justice educational program, and worked in solidarity with students and families. Second, the school’s approach to healing and transformation responded to harm at the community and individual level. Third, despite its efforts and significant accomplishments, the school encountered obstacles in building the long-term capacity of faculty and staff to meet the needs of stakeholders. Despite these challenges, RiC offers an example of education being used to forward social change and disrupt hopelessness that all educators can learn from. The conclusion explores the implications of this case study for teachers and school leaders who seek to pursue a social justice educational agenda.