Over the past 20 years, punitive approaches and policies similar to those of the criminal justice system have become prominent in our schools (Gonsoulin, Zablocki, Leone, 2012). These local, state, and federal education and public safety policies serve to remove students from the educational environment and channel them into the criminal justice system (New York Civil Liberties Union, 2007; NAACP Legal Defense and Education Fund, 2006). This phenomenon is often referred to as the school-to-prison-pipeline (STPP). Research has shown a connection between school, community, and juvenile incarceration (Christle, Jolivette, & Nelson, 2007), and indicates how providing quality evidence-based interventions can make a positive difference in the lives of youth in or at-risk of entering into the STPP (Christle, Nelson, Jolivette, 2004). The purpose of this study was to examine the writing skills of incarcerated male youth. The participants were 9th grade and 10th grade male students (N=83) incarcerated at a juvenile correctional facility. Data were collected from the students' ACT QualityCore English end-of-course assessment. Descriptive data were collected to analyze students' college-readiness. A series of ANOVAs were conducted to assess whether means on the dependent variables were significantly different among groups. The results of the study show a significant difference in students' writing mechanics skills based on grade level, and in written expression skills based on special education status. No significant differences were found in students' writing mechanics skills or written expression skills based on their participation in a creative writing program. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]