This study explores how two schools serve students who are in danger of or have already experienced the school-to-prison pipeline. The majority of students at these schools faced significant setbacks in traditional settings (e.g., truancy, poor grades, suspension, expulsion, incarceration). At each charter school, the free and reduced lunch population exceeds 90%; over half of the students have experienced homelessness; 30% are diagnosed with special needs. Results from the study show how these two schools utilize innovative programming, carefully selected staff, wrap-around services, a family-like atmosphere, and a flexible learning environment. They practice an overarching philosophy of pedagogical and institutional plasticity, an approach that is helping students to stay in school and find a sense of purpose and direction.