This chapter argues that the middle-class advantage is, at least in part, a negotiated advantage. That argument has implications for research on cultural capital, teacher bias, student resistance, and teacher authority. It also supports recommendations for researchers, practitioners, and policymakers interested in reducing class-based inequalities in school. First, I urge teachers to be sensitive to social class differences in student problem-solving. Second, I encourage schools to alleviate the challenges teachers face in assessing and responding to students’ individual needs. Third, I call on policymakers to avoid deficit-oriented programs that teach working-class students to act like their middle-class peers. Those programs ignore the fact that working-class families are often the ones complying with institutional expectations and the fact that middle-class families are the ones demanding support in excess of what is fair or required. Thus, unless educators are willing to deny such requests, middle-class children will always stay one step ahead.