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This phenomenological case study explores the college and career readiness (CCR) and postsecondary trajectories of six African American youth, 18 to 20 years of age, who attended or graduated from a northeastern urban school district during 2021 to 2022. Drawing on social reproduction theory and critical race theory, interviews, school, district and demographic data were examined to understand how participants made meaning of their CCR experiences and the family, school, work, and community influences on their postsecondary trajectories. Findings demonstrated that the youth used community cultural wealth to support their education and career goals and to navigate structures and systems. However, as participants pursued their aspirations, dominant White capital (social, financial, and temporal) in education and employment structures increasingly created barriers to their goals. Participants continued to aspire toward their dreams; however, the obstacles they confronted and their ability to navigate those obstacles varied by parental educational and occupational background. In order to ready African American youth for postsecondary success, participants recommended that CCR school implementation (a) engage with students one on one and not rely on computers; (b) ready students for good-paying jobs as well as college; (c) employ caring, culturally responsive educators and staff with high expectations; (d) offer more creative and critical thinking learning experiences and a less regimented curriculum; and (e) provide support for postgraduation transition. This research has implications for social reproduction, Black habitus, caste, and intergenerational mobility. / Urban Education