This article utilizes a qualitative case study to explore juvenile justice personnel perspectives on school reentry. Juvenile justice personnel are a little tapped into source of information on the inner workings of the school-to-prison pipeline. They provide a unique perspective as firsthand observers of the pipeline, offering a different voice and interpretation of the barriers faced by young men and women who are incarcerated in juvenile justice centers but must eventually deal with the challenges of reentering the public school system. The article begins with an overview of the literature pertaining to reentry and education and then sets out the study's objective, purpose, and research questions. This is followed by the perspective and theoretical framework informing the study; the methodology employed; the research site, participants, and sampling choice used; and the means of data collection for the study. The researchers' roles and positionalities are briefly touched on to ground the study and to ensure transparency in the authors' approach to the data. Data analysis is discussed, as are the findings and results of the study. The article concludes with implications and final thoughts on future directions for research on school reentry.