The nuances of the application of schoolwide positive behavior supports (PBS) in an urban high school setting were investigated. Impact of implementation was measured using qualitative interviews and observations, including the School-wide Evaluation Tool (SET), Effective Behavior Support Survey, Student Climate Survey, and office disciplinary referrals. The results indicated that schoolwide PBS was implemented in an urban high school setting with some success. The overall level of implementation of PBS reached 80% as measured by the SET. Staff and teachers increased their level of perceived priority for implementing PBS in their school. A decrease in monthly discipline referrals to the office and the proportion of students who required secondary and tertiary supports was noted. These findings seem to indicate that PBS may be an important process for improving outcomes for teachers and students in urban high school settings.