As privilege-dependent organizations, U.S. public schools have an interest in catering to higher-SES White families. But, what happens when privileged families’ interests conflict with schools’ stated goals? Focusing on the case of homework, and drawing insights from organizational theory, cultural capital theory, and research on parent involvement in schools, I examine how schools’ dependence on higher-SES White families influences their enforcement of rules. Using a longitudinal, ethnographic study of one socioeconomically diverse public elementary school, I find that teachers wanted to enforce homework rules, but they worried doing so would lead to conflict with the higher-SES White “helicopter” parents, on whom they relied most for support. Thus, teachers selectively enforced rules, using evidence of “helicopter” parenting to determine which students “deserved” leeway and lenience. Those decisions, in turn, contributed to inequalities in teachers’ punishment and evaluation of students. Broadly, these findings suggest privilege-dependence leads schools to appease privileged families, even when those actions contradict the school’s stated goals. These findings also challenge standard policy assumptions about parent involvement and homework, and they suggest policies aimed at reducing the power of privilege are necessary for lessening inequalities in school.