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This study examines the revision of end-of-unit math assessments in Chicago Public Schools’ Skyline curriculum to align with content standards and a district-developed culturally responsive framework. While culturally responsive pedagogy is widely discussed, few studies document how such frameworks are enacted in assessment design. Drawing on design-based research and thematic analysis, we explore how researchers navigate tensions between rigor, cultural responsiveness, and standard alignment. This work provides practical insight to sustainable, equity focused assessment design.