Based on NAEP data, many adolescents may not be adequately prepared for postsecondary education. This is a Year Five report from a seven-year longitudinal study of a student cohort starting in sixth grade year (n = 50). It uses a quasi-experimental design, and collects data from surveys, interviews, and reflective statements to evaluate mentoring strategies and outcomes. Year Five findings suggest that improvements in students' college perceptions, state mandated test scores, and high school perseverance may be associated with mentor-led initiatives including college visits, goal setting, tutoring, career investigations, role model presentations, writing projects, and presentations about college preparation and life. (Contains 2 tables and 1 figure.)