University partnerships with public schools are an innovative opportunity to marry research and practice. One such endeavor was the Heinz Fellows Program at the Center for Urban Education in the School of Education at the University of Pittsburgh. The Heinz Fellows Program existed at the intersection of community engagement, public school praxis, and university collaboration, with a pursuit of equity and justice. Yet, despite four years of programming, significant investment from philanthropy, and deep commitment from the university and public-school partners, much of the services and activities were not sustained beyond the conclusion of the program. What has remained, though, are salient lessons about the preparatory work each organization must engage in prior to collaboration. A public school is an inherently complex organization, while a university is also complex, but in substantially different ways. Thus, to bridge the chasm, both organizations must participate in self-reflection about their readiness, resources, and right constituents to implement, evaluate, and sustain the collaboration. The article offers a robust framework to consider cross-organizational collaborative readiness and to guide future university/public school partnerships into sustainability.