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We are at a critical moment for assessment in schools. Teachers are called upon to navigate advances in classroom assessment research, top-down assessment policies, and emergent crises like the COVID-19 pandemic. This paper explores teachers’ assessment challenges across contexts and analyzes teachers’ innovative responses to these challenges to support current and future assessment practices and theories. Drawing from 168 survey responses, we identify eight themes of teachers’ assessment challenges and innovations, including: obsessions with grading, time and teacher workload, limitations placed on practice, conflicting views of assessments’ purposes, the going gradeless spectrum, making learning visible, fostering assessment literacy, and lingering systemic challenges. These findings directly support the widespread goal of implementing assessments that effectively and consistently serve student learning.