Scholarship on parent-principal relationships often ignores how some parental involvement can create challenges for school leaders. We analyze parent-principal relationships at an urban public K-8 school over a 30-year period, exploring how three different principals "managed" parental involvement. Our analysis reveals how these principals negotiated relationships with parents across the shifting race and class terrains of different eras. We argue that future investigations of parent-principal relationships should focus on the tensions and challenges inherent in these relationships, as well as the effort expended and the skill required by principals to effectively manage relations with parents in diverse school communities. (Contains 7 notes.)