This study describes the characteristics of the Middle College High School, and the reasons for its success in retaining students who have been defined as potential dropouts while maintaining high graduation rates. It incorporates the perspectives of students, faculty and administrators on the issues they confront as well as the process through which Middle College improves opportunities for completing high school and attending college. Administrators and researchers who are looking for ways of improving retention and achievement of at- risk students should find it useful. Large urban communities can benefit from lessons learned as this model can be used to serve an even larger number of students. Middle College, a school-college collaborative program, brings together the New York City''s Department of Education with the City University of New York. Given the disparity between the governance structures of these two institutions, the success of the Middle College program highlights its uniqueness and is one of the most promising approaches to keeping students in school and helping them succeed.