With higher education offering a potential avenue out of a bleak alternative, School on Wheels of Massachusetts (SOWMA) has devoted countless hours to increasing the educational opportunities for young people impacted by homelessness. SOWMA first meets a student when he or she is experiencing homelessness. Once part of the SOWMA family, the student can continue to receive services for as long as he or she needs support. The "High School Plus" (HSP) program works with students who are currently homeless, as well as those who have moved from shelter to housing. This article describes how these programs have helped teens overcome the challenges of homelessness and fulfill their dreams of a postsecondary education, despite the odds against them.