This study examined patterns of (a) observed racial socialization messages in dyadic discussions between 111 African American mothers and adolescents (Mage = 15.50) and (b) mothers’ positive emotions displayed during the discussion. Mothers displayed more advocacy on behalf of their adolescents in response to discrimination by a White teacher than to discrimination by a White salesperson. Mothers displayed consistent emotional support of adolescents’ problem solving across both dilemmas but lower warmth in response to the salesperson dilemma. Findings illustrate evidence of the transactional nature of racial socialization when presented with adolescents’ racial dilemmas. The role of adolescent gender in mothers’ observed racial socialization responses is also discussed. A framework for a process‐oriented approach to racial socialization is presented.