Research on incarceration and educational access continues to reveal the stark reality for many adjudicated youth: without access to educational opportunities recidivism is probable. Yet conventional methods of teaching critical reading, writing, and thinking skills are not always successful for juveniles who have found little success (or hope) in traditional schooling. This essay argues that alternative literacy practices can effectively supplement conventional GED and vocational training courses by engaging juveniles through creativity, critical self-awareness, and a shift in how audience and authorship is understood. Research indicates that literate activity such as writing workshops, zine networks, peer and professional mentoring, and increased engagement with the publishing industry can meet the unique needs and expectations of youth offenders while also working toward the democratic principles held by many correctional educators and the general public. The essay suggests specific pedagogical approaches and practices for engaging juveniles by reviewing existing programs across the U.S. and articulates five core educational and life skills outcomes that can emerge as students learn to write beyond the sometimes limiting notion of school.