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This study examines how principals enact autonomy in their day-to-day practices. By applying the theory of street-level bureaucracy and narrative inquiry method, we conducted multiple interviews and shadowed three school principals across a full school year. We find that principals’ relationship with autonomy to be nuanced and complex. On one hand, principals used a variety of coping strategies to negotiate autonomy often feeling overwhelmed by its corresponding demands. On the other, they felt micromanaged and that they should be given greater control and authority to make decisions. By challenging the dominant reform narrative that school level authority is enough to expect effective leadership, our study contributes to understanding about the impact of autonomy on principals and their work.