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Teacher expectations are a well-documented predictor of student outcomes, yet much of the literature focuses on whether teachers hold high or low expectations rather than how expectations evolve. Drawing on ethnographic research in two progressive high schools serving low-income students of color, we argue that teacher expectations shift over time in response to structural realities, cultural logics, and daily engagement with students. We offer a nuanced view of how teachers adjust their expectations in response to both external pressures and student needs. In many instances, this leads to what we term expectations erosion—a process in which teachers recalibrate their expectations. Rather than a simple lowering of standards, expectation erosion is an evolution of reasoning shaped by cultural logics that influence how teachers assess student success, responsibility, and potential. We identify three key cultural logics—care, accountability, and success—that shaped teachers’ decision-making in both schools. While these logics often contributed to expectation erosion, school-specific logics sometimes reinforced high expectations. Teachers adjusted their expectations in real time based on student engagement, progress, and ability, making teacher-student interactions key sites of expectation negotiation. By framing teacher expectations through cultural logics, this paper advances research in three ways. First, it moves beyond static notions of high versus low expectations to show how they evolve in response to school contexts and classroom interactions. Second, it reframes expectation erosion as a meaning-making process shaped by cultural logics rather than a simple response to structural constraints. Finally, our comparative design highlights how school-specific cultural logics can counteract expectations erosion, illustrating how institutional culture shapes teachers’ responses to students in meaningful ways. In doing so, we provide a more dynamic, interactional account of teacher expectations in schools serving marginalized communities.