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Education attained after age 25 – which I call educational upgrading -- can reduce inequality by providing opportunities for disadvantaged individuals to "catch up," or it can expand inequality by allowing already-advantaged individuals to pull farther ahead. Using data from the Health and Retirement Study Life History Mail Survey, I investigate how educational upgrading reshapes educational inequality by race, class, and gender over the life course across multiple birth cohorts. I find that upgrading has been widespread throughout the 20th century, even among those born in the 1930s. Using a decomposition approach and non-parametric analyses, I show that upgrading influences inequality in educational attainment and educational timing by race, class, and gender in distinct ways. More often than not, upgrading reinforces, rather than reduces, inequalities in BA-attainment over the life course. Upgrading also results in growing inequality in the timing of BA-completion by class and race. Clearly, upgrading has been an underexamined yet consequential stage of the educational trajectory. Analyzing upgrading provides insight into how education can reinforce or undermine broader patterns of inequality and stratification.