School districts have attempted to implement many programs, initiatives, and frameworks to promote positive student behavior. However, despite these attempts, there remain inequitable student behavior outcomes in many public schools. Educational leaders who hold the position of building administrator in a public school district in Oklahoma were invited to participate in this study. This qualitative case study was context bound to a group of eight site leaders from two public high schools who consented to participate. The purpose of this study was to explore through the lens of Douglas's (1982) Cultural Theory how selected educational leaders facilitated optimal student behavior in their respective contexts. Data were collected through multiple sources, including interviews, observations, documents, and the administration of Harris's (2015) Cultural Context and Preference Assessment Tools. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]