E-SToPP’s proposed network of transformative schools and educational opportunities will be established to eradicate the school-to-prison pipeline. To date, youth at risk of or involved in dropping, suspension, expulsion, or incarceration have no viable 4-year option for graduating high school and re-entering school and community successfully through higher education, the workforce, and civic life. E-SToPP sets out to change these inequities with our bold and compelling idea of capacity-building in Miami-Dade County Public Schools to ensure successful reentry and graduation of youth in the school-to-prison pipeline. E-SToPP’s proposed network is a grass-roots effort to continually reinvent how schooling is done, which entails a (a) purposeful collaboration among all systems; (b) transparent and effectively operationalized educational trajectory; and (c) grounding in Transformative Literacy Pedagogy. It offers youth timely and unique support mechanisms when their educational trajectory is disrupted through referral, suspension, expulsion, or incarceration. At each touchpoint of disruption, E-SToPP envisions (a) virtual, mobile, and face-to-face mentoring support; and (b) school- and community-wide support that operates as a comprehensive family-community teaching-learning outreach-reentry hub and resource center to serve the unique needs, strengths, and goals of its youth, families, and communities. Grounded in its transformative conceptual purposes, core values, and guiding principles, E-SToPP’s “safe haven” reentry model of empowering and preparing youth who have been disproportionately funneled into the school-to-prison pipeline with excellent equitable education has the potential to transform high school learning and to launch a nationwide trauma-informed continuum of care model for our society’s schools, including the process of navigating youth through disrupted educational trajectories to successful reentry, graduation, and beyond.