This case study examined the influences of autonomy and uncertain expectations of accountability on the functioning of an urban charter school during its initial years of development. The school studied was a charter school in its second year of development that was attempting to measure student improvement in challenging areas such as social adjustment and interpersonal behaviors while working with a challenging population of at-risk high school students. Data were collected from a variety of sources, including interviews with the schools staff of four teachers, a counselor, a classroom assistant, and the school director. Documents generated by and about the school were also studied. Findings show that while requiring schools to administer assessments for purposes of documenting accountability is a worthy goal, the usefulness and appropriateness of such efforts are contingent on knowledgeable decision making. There were a number of problems in the start-up of this school, and findings show that it will be increasingly important to reexamine the notion of charter school autonomy so that the freedom to be creative and innovative does not collide with the need to be responsible and accountable. (SLD)