A university and a large urban district began collaborating in 2003 to intensify and customize the preparation of principals. District leadership viewed the principal as the keystone to improving academic achievement for all students. The university and district reciprocally collaborated on the design and implementation of this principal preparation program. From 2005, a case study research design consisting of document review, surveys, interviews, and observations has provided ongoing data for program development and district information. The experiences of the new leaders have informed both systems of their current organizational cultures and the barriers and levers for second-order change. (Contains 1 figure and 2 tables.)