This paper argues that inequalities can be more clearly understood by combining tool kit theories of culture that stress convergence between institutional expectations and individual behavior with symbolic interactionism, which emphasizes the interpretive and situational nature of behavior. I base these arguments on an ethnographic analysis of student responses to ambiguous expectations around help-seeking. Teachers’ shifting expectations created interpretive moments, to which middle-class and working-class students responded differently. Through a logic of entitlement, middle-class students saw ambiguities as opportunities for reward and tried to seek assistance. Through a logic of appeasement, working-class students saw ambiguities as opportunities for reprimand and sought to placate teachers by avoiding requests. Teacher responses to student behavior varied across situations but helped to perpetuate inequalities. Such findings suggest that the activation of tool kit resources and the stratified profits that result are more interpretive and situational than scholars typically acknowledge.