Residential segregation by race and class is a durable form of inequality. Yet, we know less about how the unequal sorting of families into neighborhoods and schools occurs. Drawing on interviews with a diverse sample of 156 families, we examine whether residential and school decisions are connected and how they differ by household income. We find that, for higher-income families, residential decisions maintain and build on existing educational advantages, while lower-income parents churn between both houses and schools, doing the continuous work of compensating for unequal settings. Only the highest income—mostly White—parents report that they can combine their housing and school decisions and achieve satisfaction in both domains. In contrast, housing insecurity and unequal, racially-stratified geographies constrain less advantaged, primarily minority families to prioritize affordable shelter over school choice. When such trade-offs lead to inadequate educational experiences for their children, these families try to improve their children’s schools through re-optimization strategies, withdrawing and re-enrolling them into different schools. While some parents perceive that these changes benefit their children, such school transfers can also increase educational instability. More generally, the lack of quality schools in affordable neighborhoods burdens families by requiring compensatory strategies to resolve housing and educational shortcomings.