Although policies aiming to increase school-based autonomy are commonplace, we know little about how school actors use autonomy to improve organizational performance in varied contexts. This paper surfaces perspectives from school leaders and teachers on the effectiveness of autonomy and describes how these perspectives vary across schools. We use contingency theory to guide our analysis of case study data from eight schools in the Denver Public Schools (DPS) district which vary in school governance, performance, and demographics. We interviewed school principals, teachers, teacher leaders and other charter and district administrators in the 2016-17 school year, totaling 53 participants. School cases consistently reported high levels of accountability pressure from the district central office to improve student test scores that, in turn, informed their mission and goal setting. Schools also reported different levels of autonomy that varied according to school governance model and consistently described these levels as optimal for achieving school goals. Several internal and external contingencies shaped these perceptions albeit in different ways depending on autonomy level. Relevant contingencies included task uncertainty in each school's mission, teacher organizational fit, school leadership, support from intermediate entities, and procedures to coordinate decision-making across school actors or organizational sub-units.