The authors examined relationships between cultural socialization and preparation for bias and youth outcomes. Using data from 805 African American and White early adolescents attending school in an integrated middle-class suburban school district in the northeastern United States, the authors hypothesized that ethnic affirmation and self-esteem would mediate relations between ethnic-racial socialization and more distal academic and behavioral outcomes. Cultural socialization was positively associated with academic and behavioral outcomes, and these associations were partially mediated by ethnic affirmation and self-esteem. Preparation for bias was associated with more negative academic outcomes, and these relationships were fully mediated by ethnic affirmation and self-esteem. Relationships of preparation for bias to youth outcomes were generally stronger for White compared with African American youths. The risks and benefits of different socialization messages for youths in various ecological contexts are discussed.