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Research confirms the extent of school segregation, yet the path forward remains elusive. This paper evaluates the goals of stakeholders working to address issues resulting from school segregation and demonstrates that existing quantitative tools fail to adequately assess progress towards achieving these goals. Using common tools, this paper analyzes five years of enrollment data in New York City’s public schools and finds that trends in diversity and segregation are muddled by measurement. This analysis also highlights the lack of quantitative tools for assessing equity and inclusiveness—two goals central to key stakeholders’ theories of action. The paper argues that scholars must develop new measurement tools that meet the needs of stakeholders, and it concludes by offering a few such tools.