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Anchored in Pinar and Grumet’s (1976) currere, this collaborative critical autoethnography enlisted four student-scholars and two high school teachers, each of whom selected a pivotal memory exemplifying the school-prison nexus. After tracing regression, progression, analysis, and synthesis, we added a fifth movement—bridging—in which students backward-engineered from imagined liberatory futures to specify curricular, pedagogical, and relational shifts. Through journaling, poetry, and dialogic counter-storytelling, students asserted analytic authority, excavating genealogies of carcerality while charting futurist levers—re-humanizing praxis, community co-design, and inclusive governance. Findings show that positioning students deemed inmates within the school-prison nexus as researchers, through critical qualitative methods that honor their wisdom and speculation, yielded qualitatively different insights and a practical roadmap for moving schools from containment toward collective liberation.