Many students approach the transition to secondary school with feelings of both excitement and apprehension, but it is excitement that usually prevails. For students with Asperger's Syndrome, however, those aspects of secondary school that most students anticipate with great enthusiasm, such as being in a new and larger environment, having different teachers and increased subject choices, and meeting new people, are sources of great anxiety. Despite the increasing numbers of students being diagnosed with Asperger's Syndrome (Safran, 2002), many teachers have limited understanding of the condition, or of appropriate strategies for the successful inclusion of students with this diagnosis (Williams, 2001). This paper examines aspects of secondary school that are particularly challenging for students with Asperger's Syndrome and describes ways in which these issues were addressed by teachers who approached these challenges with flexibility and ingenuity.