This study examines the case of one large urban school district's implementation of Positive Behavioral Interventions and Supports (PBIS) to review competing needs and challenges encountered over a four-year period. There are encouraging results supporting the finding of a successful PBIS implementation and plans for continued implementation of Tier I practices and expand Tier II supports. Reducing the continuing disparity between the percentages of African American and White students receiving disciplinary consequences remains a challenge for Middleton ISD. In addition, work remains to reduce the disproportionate number of students receiving special education services who receive higher levels of disciplinary consequences.