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Triggering events and the scarring, or status-dependence, process they induce are an important cornerstone of social stratification theory that is rarely studied in the context of the educational career. However, the decades-old high-stakes environment that ties many educational outcomes to a test score or other singular achievement underscores the potential importance of scarring in the contemporary educational career. In this paper, I study scarring in the educational career in the case of primary-grade retention. Using propensity score matching and sibling fixed-effects models, I evaluate evidence for primary-grade retention effects on high school completion and college entry and completion. I find consistent evidence of a causal effect of early primary school grade retention on high school completion. These effects operate largely through middle school academic achievements and expectations, suggesting that students who recover from the scar of grade retention on high school completion largely do so earlier rather than later in the educational career. Students can continue to recover from the effects of grade retention through early high school, not only through their academic achievements but through their expectations of high school completion as well. Models suggest that early primary grade retention scars the educational career mainly at high school completion, though there are important, unconditional effects on college entry and completion as a result. I conclude by placing these findings in the larger grade-retention literature and discussing future research on heterogeneities in and mechanisms of retention effects.