What roles do parent and family engagement and community outreach play in educator efforts to improve low-performing urban schools? To address this question, we considered findings from our 3-year case study of Brookdale Elementary (a pseudonym), which was undergoing a state-mandated, district-directed turnaround reform effort from 2011 to 2014. Specifically, we investigated how and why school personnel engaged with and reacted to parents and families, community-based organizations, and the surrounding locale. In the end, the school's educators encountered complicated obstacles yet generated some tangible victories in their pursuit of productive school, parent/family, and community connections. We conclude by considering implications of our findings.