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Research has continually indicated that teachers face systemic challenges to their assessment practices, including using assessment to support diverse learners and navigating technology. This study examined factors shaping teachers’ perceived frequency and significance of six core assessment challenges as identified in previous research. Data were collected from 368 teachers via an online survey. We identified significant correlations between the perceived frequency and significance of each assessment challenge and demographics, teachers’ approaches to assessment, assessment-related emotions, and associations between teachers’ approaches to assessment and assessment-related emotions. Teachers who endorsed student-centric approaches to assessment were more likely to report positive assessment emotions and perceive assessment challenges as more frequent and significant than those endorsing teacher-centric approaches.