College transition programs offer early access to the collegiate experience, aid in the adjustment of students transitioning to college, and facilitate positive adjustments for Black women in their early college years. Less is known about whether Black women identify these programs as having a lasting influence on their college degree programs and careers. This critical oral history study of 24 Black alumnae contemplates their recollections of how college transition programs influenced their collegiate journeys within predominantly White and historically Black institutions. The Black alumnae emphasized the long-term importance of asset-based community cultural wealth approaches in transition programs that offered a head start to college. The alumnae noted that the transition programs provided forms of navigational, aspirational, and social capital. At PWIs, transition programs emphasized academic skills and social networks. At HBCUs, transition programs offered inclusion in the familial ethos of those campuses. In both institutional types, the women enjoyed gaining confidence and access to a hidden curriculum, which they retained throughout college and into their careers and lives.