Making postsecondary education more accessible has highlighted the issue of what it means to be prepared for college. A significant number of students enter college with preparedness issues--academic and otherwise--that challenge potential success. For African American students, educational, social, and economic factors combine to create barriers that are often more acute and therefore more difficult to overcome as they strive to negotiate the intricate fabric of elements associated with completing college. This article describes the development and implementation of a comprehensive summer transition program at an HBCU that attempts to weave a seamless strategy of preparation and acclimation that will enhance academic readiness, self-efficacy, skills, and habits necessary for college success. This highly structured approach is generating practices that could become key factors in improving retention and graduation rates.