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This thematic literature review examines how situative learning theory shapes the design and evaluation of assessments in online and open learning environments. Based on over a decade of design-based research, we introduce a three-dimensional framework that reinterprets key assessment features—principles (validity, reliability, fairness), formats (e.g., selected vs. constructed response), and levels (immediate to distal)—through a situative perspective. We show how expansive framing, personal authenticity, and participatory learning structures transform assessment to better promote learning transfer and equity. Our analysis aligns with the 2026 AERA theme by suggesting assessment practices that challenge exclusionary norms and create new educational opportunities. We end with recommendations for designing assessments that acknowledge learners’ diverse identities, experiences, and paths.