This article explores the connection between dropping out of school and being incarcerated, particularly for youth, including students from culturally and linguistically diverse backgrounds, students from poverty, and students with disabilities, who have been shown to be at higher risk for both. This article seeks to shift focus away from a deficit-based perspective and instead creates an integrated learning model that incorporates culturally responsive teaching with an integrated services model in order to promote access, equity, and culturally supported experiences for children. If students are supported and successful in school, then dropout and incarceration should decrease and the pipeline from school to prison can be broken.