In this study I argue that educational practitioners and policy makers cannot solve the problem of increasing student learning and growth by organizationally isolating the work of schools from communities. The purpose of this study was to explore which organizational conditions have enabled and which have hindered schools and communities from successfully working together to help students learn and grow. In addition, I explore why some districts and schools continue to struggle with engaging outside stakeholders despite their efforts. I used a comparative case study design and chose to investigate three districts and two schools within each of those districts in order to see how district engagement policies and practices filter down into schools. I used neo-institutional and organizational theories as conceptual tools. Results showed that district level engagement efforts were loosely-coupled with school level policies and practices. Policies that did exist around engagement were vaguely worded and weakly monitored. In addition, formal policies for engagement were weak and few innovative approaches existed to actively engage outside stakeholders. This study confirms the neo-institutional framework and its usefulness in examining engagement policies and practices. [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/en-US/products/dissertations/individuals.shtml.]