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In this paper, we draw on theoretical perspectives from QuantCrit, LatCrit, AsianCrit, and segmented assimilation to argue that historical contingency of immigration is a critical piece missing from many quantitative analyses of race/ethnicity in education. Using data from the Children of Immigrants Longitudinal Study, we demonstrate the importance of immigration context by comparing educational outcomes between children of pre- and post-Mariel Boatlift Cuban migration waves to South Florida. Post-Mariel migrants faced negative public images and fewer social resources upon arrival than pre-Mariel migrants. We find suggestive evidence that children of post-Mariel migrants attended lower-quality schools and had lower educational attainment than children of pre-Mariel migrants, further suggesting that parents’ immigration context was associated with different educational trajectories for children.