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The need to ‘iterate’ is now commonplace in implementation literature. However, there is little empirical research into what iteration looks like in K12 education. In this paper, we draw on a multi-year study of four school districts implementing diverse iterative approaches, including improvement science, design-based implementation research, DataWise and design thinking. By studying these methods collectively, we document the common challenges of iteration and analyze their sources. We find that iteration occurs relatively rarely, and trace this to the fact that it relies on not one, but two demanding processes: 1) collecting and interpreting feedback and 2) engaging in and acting upon new professional learning. We conclude with steps for districts to take a multi-layered approach to developing iterative capacity.