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Educational accountability policies are a popular tool to close the achievement gaps between advantaged and disadvantaged students. However, these policies may exacerbate inequality if families from advantaged backgrounds are better able to advocate for their children and thus circumvent policy. We investigate this possibility in the context of the early grade retention policy in Florida, which requires all students with reading skills below grade level to be retained in the third grade, yet grants exemptions under special circumstances. We find that Florida’s third-grade retention policy is in fact enforced differentially depending on children’s socioeconomic background, especially maternal education. Holding exemption eligibility constant, scoring right below the promotion cutoff results increases the retention probability 14 percent more for children whose mothers have less than a high school degree as compared to children whose mothers have a bachelor’s degree or more. We also find that the discrepancies in retention rates are mainly driven by the fact that students with well-educated mothers are more likely to be promoted based on subjective exemptions such as teacher portfolios.