As a result of various academic, behavioral, and social-emotional challenges that adolescents may experience during high school, an alarming rate of students are not acquiring their high school credentials. To address this concern, researchers have suggested dropout prevention efforts should focus on using a comprehensive, preventative, tiered framework such as Schoolwide Positive Behavior Interventions and Supports to target alterable classroom-level variables such as student behavior, student attendance, academic performance, and student engagement. One of the most efficient and effective methods for improving academic engagement and student behavior is through the implementation of evidence-based classroom management practices, such as increasing students' opportunities to respond (OTRs) during teacher-directed instruction. Unfortunately, many teachers lack adequate amounts of training in these practices. In a single-case, multiple baseline design across two teacher participants, this study investigated the effects of multilevel professional development (PD) and coaching support provided by a school-based coach on high school teachers' use of a trained classroom management skill (i.e., OTRs) during teacher-directed instruction. Overall results showed teachers improved implementation fidelity but failed to achieve the required rates of OTRs. Additionally, when teachers improved implementation fidelity, students also demonstrated increases in active academic engagement. Social validity data indicated teachers and the school's instructional coach rated the multilevel PD and coaching framework to be moderately effective in supporting teachers' implementation of high rates of OTRs. Student participants reported observed increases in teachers' use of a variety of OTRs, positive feelings associated with actively participating in class when presented with increased OTRs, and a better understanding or retention of course content when teachers used high rates of OTRs. Limitations of the study, implications for practice, and suggestions for future research are discussed. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]