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This paper examines the causal effects of grade retention on educational trajectories using plausibly exogenous variation from Chile’s nationwide attendance-based promotion policy. Employing a fuzzy donut regression discontinuity design, I find that marginal retention increases high school dropout rates by 22%, with heterogeneous effects: the impact is four times larger for students whose mothers are high school dropouts compared to those with college-educated mothers, but no gender differences emerge. I document strategic manipulation of attendance records by schools, particularly those serving disadvantaged students, attenuating retention’s negative consequences for the most vulnerable. By analyzing retention timing across primary and secondary education, I provide a unifying framework for understanding its dynamic effects: retention in early grades has minimal impacts, but later retention reduces high school completion and shifts students toward adult education. However, conditional on college exam participation, high school retention improves performance by 0.1 standard deviations, suggesting potential long-term trade-offs. These findings reconcile mixed evidence in the literature and highlight the importance of policy design in mitigating unintended consequences.