Can poor student performance on high-stakes assessment, including high school exit exams, indicate gaps in school and district curriculum and instruction? How might this affect students identified with special needs, and what could it mean in terms of a free and appropriate public education? This case illustrates how a student receiving special education services progressed in a school system with accommodations and modifications, only to fall short on a high-stakes exam at the end of his school career. The study explores what challenges this poses for the individual student as well as the entire school system and its leaders.