Colleges are under mounting pressure to increase retention rates by easing incoming students' academic and social transition to college. Finding time in first-year students' busy schedules to provide this additional support can be difficult, however. Thus, the Clipper Project set out to test whether offering online, college level courses to high school seniors might be one way postsecondary institutions could "reach out" to incoming students and help them begin their transition to college before matriculation. We found that early engagement with the University can help participants adjust more quickly, but the best time to engage incoming students may not be during the second semester of the high school senior year. (Contains 9 tables.)