Partnerships between universities and school districts are increasingly being identified as a means to overcome the difficulties of preparing the next generation of urban high school principals. This article examines the development of such a multiorganizational partnership with a large urban school district, two universities, and a national educational organization. The partnership development is analyzed against a framework of dimensions of effective collaborations. Data include interviews and observations and are analyzed using qualitative methods. Findings indicate that challenges in multi-institution partnerships are inevitable. However, the overarching focus on a common goal, defined responsibilities, authentic communication, alignment of common interests, and dynamic receptiveness to ongoing evaluative feedback enables the sustenance of an effective program.