The overuse use of punitive consequences in response to aberrant student behavior has become a focus of attention for policymakers, practitioners, and researchers. Its use appears to be having a detrimental impact on students and their futures. The present study examined practices designed to reduce the number and nature of these punitive approaches used in high-poverty urban middle schools. Furthermore, the literature confirms that African American males receive a disproportionately high percentage of punitive disciplinary practices and that the impact on these students and their future is a concern for schools and society. The present study was conducted at a school in which the number and percentage of disciplinary actions were higher than for similar schools in the district and in which those actions applied to African American males were also disproportionately high. Guided by the literature, the nuances of the first 36 months of a school-wide implementation of Positive Behavioral Interventions and Supports (PBIS) were investigated. The impact of implementation was measured using qualitative interviews, observations, the School-wide Evaluation Tool (SET), the Effective Behavior Support (EBS) Survey, and Office Discipline Referrals (ODRs). The results indicated that school-wide PBIS was implemented with some notable success. School-wide PBIS implementation was measured by the SET at 80% after the first 36 months. Teachers and other staffers increased their level of priority for implementing PBIS with fidelity in their school. There was a decrease in both monthly and annual discipline referrals to the office (the latter dropping from 1,360 to 695) over a 36-month period of time, and the number of disciplinary referrals applied to African American males also decreased (dropping from 444 to 256) during that same period. However, African American males continued to receive a disproportionately high share of those reduced actions. They represented 18% of the student population but received 36% of the disciplinary actions. These findings seem to indicate that the implementation of school-wide PBIS may be an important process. However, as the model continues to be implemented, better and more proactive support for African American males is needed.