Many educators consider the final year of high school to be a "vast wasteland," an epidemic of disengagement. Although high schools across the country have struggled with senioritis, responses to the problem have largely fallen into vertical acceleration, in which schools typically offer an array of AP courses or dual enrollment opportunities; remediation, in which the senior year is viewed as the last time to address deficits before pursuing post-high school endeavors; and structured containment, in which the solution is simply to batten down the hatches and maintain the status quo. Although all three responses may be useful to some degree, they offer limited success because they ultimately fail to take into account who seniors are and what they need. New Trier High School in Winnetka, Illinois, recognizes the need to engage seniors constructively and, more important, to prepare them for the world beyond high school, whether college or the workplace. In this article, the authors discuss the four initiatives adopted by New Trier High School to create a dynamic senior year experience: (1) a student-driven guidance program that culminates with a daylong senior institute; (2) a classroom mentoring model, which places seniors in classrooms across the curriculum to assist teachers and students in a variety of ways; (3) a five-week experiential education opportunity during the final quarter of senior year; and (4) a yearlong service-learning project with Habitat for Humanity.