This study examined how the racial socialization process of at-risk African American female eighth grade students and their parents/guardians influences their racial identity and middle school experiences. During the stage of identity formation, adolescents seek independence from their parents and desire acceptance from their peers. A basic qualitative interpretive approach was utilized for this research design with racial socialization and critical race feminism as the theoretical frameworks. Four at-risk African American female eighth grade students and four African American parents/guardians were interviewed, to understand how racial socialization of parents influenced students’ identity formation and academic achievement. Documents such as report cards and disciplinary referrals were reviewed to confirm or refute the data obtained through the interviews. Data analysis utilizing memos, categorizing, and document analysis, produced five themes: Cultural Preparation for School, Advocating and Developing Racial Identity, Importance of Self-Awareness, Middle School Life, and Adolescent Black Identity Development. The findings of this study suggest that at-risk African American female eighth-grade students’ greatest challenge racially will come from their efforts to acculturate to the White Euro-American school culture and the influence of popular culture. In addition, they should be ready for challenges related to strained relationships with middle school teachers and administrators.