Although a growing body of literature is produced on reform of urban school districts, few studies examine shifts in the culture of managers resulting from reorganization in these bureaucracies. This article engages an analysis of central office managerial culture in the New York City Department of Education during a culminating moment of district office restructuring. I argue that a lack of consistent practices ensuring inter-office network building was instrumental in shifting the prevailing culture of the central office from an instruction-based to an accountability-based organization. Managerial restructuring was coordinated by way of empowerment, technology, and the use of space. I label this arrangement entropic, arguing an order through disorder as innovation, constraints from the district's organizational environment, and uncertainty lead to a focus on performance conditions more than institutional capacity. The study draws on ethnographic research and in-depth interviews conducted with upper and middle managers of this school district.