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The analysis that uses the National Longitudinal Survey of Youth 1997 (NLSY97) data suggests that unfavorable labor market conditions at the time of leaving high school increase college enrollment one year after high school. The analysis that uses the Current Population Survey (CPS) data shows this effect has varied significantly over cohorts/generations of the past 40 years. The empirical results from analyzing the NLSY97 also indicate that the positive impact on college enrollment in the short run also translates into positive effects on achieving more educational attainment, either in terms of completing more years of college or attaining a college degree six years after high school. Overall, these effects are not strongly heterogeneous between the sexes; however, these effects are highly disproportional across race/ethnicity and ability subgroups.