High dropout rates among students who repeated grades are often cited as evidence that grade retention is harmful. This article uses event history analysis to explore whether and how a grade retention influenced graduation outcomes among one cohort of youths from an urban school system. Repeating a grade from kindergarten to sixth grade was associated with a substantial increase in the odds of dropping out even after controlling for differences in background and postretention grades and attendance. This article explores whether grade retention may influence school dropout because it makes students overage for grade. Students who ended sixth grade overage for grade experienced substantial disengagement during middle school; nearly one quarter dropped out, and those who remained had significant declines in attendance. I find that the impact of being overage for grade during adolescence may explain a large proportion of the higher dropout rates among retained youths.
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