The authors' conception of a Professional Development School has been in the making for six years; they have nurtured their high school/university partnership over that period of time with little involvement from other university personnel. Through a self-study approach, they investigated the intricacies of how professional relationships, both in and out of academia, evolve and inform our practice within the partnership. In this article, they address the challenges involved in expanding the professorial roles of PDS activities within an existing school and subsequently adding another. While they believed their philosophies and ideas of working with and in the schools was a shared vision among the university faculty involved, they realized that it was a much more complex task than originally conceived.