Many students enter large comprehensive high schools without having the necessary social and academic skills or understanding of what will be expected of them as they move through the high school curriculum. To help a higher number of students experience success, schools must help them develop academic, social, and self-management skills. Collaboration between a sending middle school and a receiving high school results in supported transitions for rising freshmen. Cheltenham High School and Cedarbrook Middle School, sending and receiving schools in the School District of Cheltenham Township, are within walking distance of one another in the suburbs of Montgomery County in Wyncote, Pennsylvania. The schools have jointly developed a multilayered approach to curtail some of the problems that arise when students start ninth grade poorly prepared for high school, such as ninth-grade dropout rates, poor attendance, discipline problems, and retention. (Contains 5 resources.)