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The COVID-19 pandemic upended all aspects of societies around the world, including major interruptions to educational assessment systems. Additionally, racial inequities were brought to the forefront of social conscience, highlighting educational inequalities. This study explores how contextual race and economic factors may relate to and explain measurement challenges that possibly arose during schooling changes in 2020 and beyond. We fit a series of multilevel models to explore racial and economic school-level factors in assessment data alongside psychometric problems of differential item functioning and person fit in classroom assessment measurement models. Methods and results demonstrate ways our project’s classroom assessments were impacted by the “twin pandemics”, emphasizing the importance of evaluating such concerns to ensure valid interpretation of classroom assessment data.