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Grade retention in Chile has historically been tied to notions of merit and effort attributed to students and their families; despite a recent reform that removes automatic retention criteria, entrenched beliefs support the practice. Through a document and thematic analysis of Ministry of Education decrees (1925–2018) and educational magazine articles (1928–2023), we found historically discontinuous shifts between high and low acceptance discourses of grade retention linked to assumptions regarding who is responsible for school failure. Despite policies promoting student well-being, entrenched beliefs fed by these norms and discourses of high acceptance of grade retention, sustained it for decades, normalising it as a strategy for managing heterogeneity. We discuss the implications for policy reforms promoting inclusivity and student well-being.