Research supports the difficulties that students with Asperger's Syndrome (AS) and High-Functioning Autism (HFA) have in developing successful interpersonal relationships. While they want to establish friendships, students with AS fail to recognize and accurately interpret social cues and verbal and nonverbal behavior (Iovannone, Dunlap, Huber, & Kincaid, 2003). Social situations become even more complex as these students enter adolescence and learn that unspoken social "rules" vary within different environments, situations, and cultures (Myles and Simpson, 2001). Thus, developing social competence is critical for future success (Howlin, Goode, Hutton, & Rutter, 2004). The Oakstone Challenge (TOC) is multi-dimensional approach that combines the use of contextual self-monitoring and community building to teach and promote the generalization of social skills and in adolescent students with AS. A theoretical basis and program description of TOC are provided. Future implications for the development of social competency with students with AS are discussed.