The purpose of this case study was to explore the context and key features of a successful decade-long district and university principal preparation program. Despite the importance of such partnerships, long-standing partnerships appear to be far from the norm. The partnership was designed in collaboration with faculty at a flagship university in the American Southwest and district leaders in a large urban school system. At the initiation of the partnership, the school district faced challenges similar to other districts in ensuring a steady pool of quality school leaders. The study was grounded in theory and anchored in relevant scholarly literature. Research methods included data collected from a qualitative analysis of the perspectives of key personnel who co-created the principal preparation program and supplementary data from external evaluations conducted by recognized appraisers. Findings indicate that district-university partnerships are more likely to endure when the partners are able to strengthen shared goals, leverage existing assets, sustain trusting relationships, uphold mutuality of purpose, and support collaborative interactions. The implications and recommendations from the study may appeal to other providers of principal preparation programs who desire to adapt the lessons learned and build on the assets that exist in their own unique school and community contexts. Future research on long standing district-university partnerships may help inform states in their oversight of principal preparation programs and university and district partners who wish to start or sustain the recruitment, preparation, placement, and retention of quality educational leaders in contextually specific and complex school environments.