There is increasing pressure on the central office, particularly in large school districts, to improve student outcomes across schools and to close large achievement gaps between groups of students based largely on race and income (Louis, 2008; Honig 2012). Reforms intended to "raise the bar and close the gap" in student achievement are often implemented at the intersection of central office and schools. However, these efforts often do not achieve their intended outcomes. In this context, it is essential to understand the conditions under which reforms targeting the central office-school relationship succeed or fail. Given the pressing need for improved approaches to managing school systems, my dissertation explores the relationship between school leaders and central offices in two large, urban districts in Maryland. I use a qualitative inquiry strategy that incorporates interviews and document review to construct case studies of principals' interactions with central office in the two districts. (Yin, 2013). I then use the framework of loose coupling theory (Orton & Weick, 1990; Wieck, 1976) to interpret the conditions under which the central office-school relationship leads to consistent or variable practices across schools. In the case studies, I examine three essential functions--budgeting, staffing, and academic programming--shared between principals and central office (Johnson, Marietta, Higgins, Mapp, & Grossman, 2015). I found that the two school districts took fundamentally different approaches--one centralized and the other decentralized--to managing their relationships with schools in the three functions. As a result, principals in each district had very different interactions with central office as they carried out their work. Examining these interactions through the lens of loose coupling theory sheds light on whether the districts' approaches worked as intended. Under some conditions, the approaches worked as expected (e.g. centralization produced tight coupling). However, in other cases, the approach did not (e.g. centralization led to loose coupling). Two factors appeared to matter the most in determining whether an approach worked as intended: the capacity of principals and principals' perceptions of the capacity of central office. Findings from the research show the importance of matching the district's approach to capacities of those responsible for implementation. [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.]