Urban middle school students of color are disproportionately subjected to exclusionary discipline, reflecting a discipline gap between White students and students of color. The discipline gap results in negative outcomes similar to those caused by the academic achievement gap. Although the discipline gap occurs at all levels of schooling, it becomes exacerbated at the middle school transition when all students are subject to exclusionary discipline more frequently than they were in elementary school. Some students experience repeated discipline events throughout the school year causing them to become persistently disciplined. Although persistently disciplined students are frequently subjected to discipline experiences, they are rarely asked their perceptions of these experiences. Drawing upon stage-environment fit theory, this qualitative study examines the experiences of 11 persistently disciplined urban middle school students of color to understand how they experience the middle school transition, how it adversely impacts them, and how it contributes to the rise in the discipline gap at this developmental stage. Findings suggest that peer "drama" plays a key role in derailing persistently disciplined students and attention to peer relationships will be required in successfully decreasing discipline events. Additionally, these students require rigorous content be made accessible to them by supportive teachers and through means that do not require the mastery of reading.