Placing prison abolition on the horizon for scholars committed to interrupting the flow of young people toward prisons and jails, this article offers movement analysis, frameworks and associated questions surrounding advocacy and engagement. First, I offer a brief state of the field of research and advocacy surrounding school-to-prison work. Building from this assessment, I identify four ongoing tensions within this field that is, by definition, theoretically explicitly linked to advocacy for justice. Our challenges include exceptionality, specifically our desires to center children and youth in our analysis and organizing, and concurrently how carceral practices continue to change the face of the state and require us to track how alternatives to incarceration are defined and organized. We also struggle to build sustainable and viable decarceration initiatives and to develop ways to make schools and communities safer, without augmenting a carceral state, and to address state and interpersonal violence, while integrating an intersectional analysis that includes lesbian, gay, bisexual, transgendered and queer lives and feminist standpoints. Finally, I close with a push for scholars to continually evaluate professional investments, and invite readers to consider how our scholarly locations augment or constrain our ability to participate in building transformative schools and communities.