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Teacher expectations are a key predictor of student outcomes, yet how they evolve over time remains understudied. This ethnographic study of two progressive high schools serving low-income students of color examines how teacher expectations shift in response to structural realities, cultural logics, and daily interactions. We identify three cultural logics—care, accountability, and success—that shape teacher decision-making and contribute to expectation erosion, a process in which teachers recalibrate expectations based on student engagement and progress. Rather than simply lowering standards, expectation erosion reflects a shift in reasoning shaped by institutional culture. By moving beyond static notions of high or low expectations, this study offers a dynamic, interactional account of how teacher expectations are constructed, contested, and transformed in practice.