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Despite prevailing narratives about the near impossibility of education reform as a result of teachers union power, many US communities with strong teachers unions have experienced significant educational transformation over the past decade. To understand this surprising phenomenon, this comparative case study leverages rich interview and documentary data from six purposefully selected cities with strong teachers unions and divergent histories of education reform to clarify the challenges and opportunities of educational change in high-labor communities. In doing so, it identifies several political, social, and organizational factors associated with education reform success and failure in high-labor communities as well as issue areas containing the most promise for reform. This paper concludes by discussing implications for education researchers, policymakers, and leaders.