ABSTRACT: Cash-strapped municipalities throughout the United States are increasingly proposing innovative education policies linking school-based reforms with neighborhood-level interventions. Boston is one such city. In this paper, we describe, analyze, and critique the City of Boston's “Circle of Promise” initiative, a holistic education policy designed to coordinate school reforms with local community-based organizational resources. We link our discussion of challenges and critiques with the term “institutional entrenchment,” referring to institutional barriers to successful urban policies and the defense of the status quo. We conclude with suggestions for future policy to overcome the impediments of institutional entrenchment, and by extension, improve educational opportunities for students in underperforming urban schools.