This study’s purpose was to learn why some youth who participated in the Strong African American Families (SAAF) program increased alcohol use after 2 years whereas other youth did not. Using a sample of 28 African American caregiver-youth dyads, the authors collected qualitative data to explore these issues. Findings underscore the importance of caregivers’ practicing vigilant monitoring to keep their adolescents from experimenting with alcohol. Recommendations for limiting access to alcohol and encouraging vigilant parenting are discussed.