During a school day, children make several transitions between activities, which can take away from instructional time and result in challenging behaviors. This study investigates the impact positive engagement and behavioral supports have on children's behavior while transitioning. Participants (N = 40; 77.5% Male; 92.5% Hispanic) were enrolled in the Summer Treatment Program for Pre-Kindergarteners, a school readiness program for children with externalizing behavior problems. Using a between-group, cross-over design, classrooms were randomly assigned to three conditions: (a) silent monitoring (i.e., children and counselors transitioned silently or quietly), (b) positive monitoring (i.e., counselors provided praise and children were allowed to talk), and (c) positive monitoring and engagement (i.e., counselors provided entertainment and praise). Results demonstrated significant differences in rule violations based on the transition condition, where groups receiving positive monitoring or engagement displayed fewer violations than those receiving silent monitoring. Implications for educator practices and school policies are discussed.