Principals are critical to the effectiveness of schools, especially those serving children with the fewest advantages in life. So how can it be ensured that principals have the skills to carry out this challenging and evolving job? Enter the powerful combination of university principal preparation programs and the school districts their graduates feed into. Since 2016, the University of Connecticut has been part of an effort, supported by The Wallace Foundation, that seeks to improve principal preservice training. A centerpiece of that work is the development and operation of university-district partnerships, from start to finish. Alongside the Connecticut Department of Education, the University has worked in partnership with Meriden Public Schools, Hartford Public Schools, and New Haven Public Schools. The latter two are the second- and third-largest districts in the state, respectively, but all three are urban districts serving a high number of students from low-income families. In this article, the authors share how their experience in the University Principal Preparation Initiative shifted their mindset about the work they do with school districts from a transactional to a transformational partnership. Herein, they describe some important lessons in their collaborative journey to enhance principal preparation in Connecticut.