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There has been widespread concern about widening educational attainment gaps between children from upper- and lower-income families as income inequality has increased. This study examines the phenomenon of “delayed” college enrollment, defined as enrollment more than two years after a cohort’s graduation year, to understand how it affects trends in income-based gaps. This study is situated in the frameworks of income stratification and life course perspective. Results indicate that delayed enrollment increased between 1992 and 2004 among students from low-income families but not among students from high-income families. Consequently, the estimated change in the income gap in enrollment was sensitive to when enrollment was measured. Implications of these trends in relation to the frameworks are discussed.