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Earning industry certifications helps people prepare for jobs in a range of careers. Doing so in secondary school may help students prepare for college. Using administrative data on two cohorts of first-time ninth graders from Florida, we examined whether earning a certification was associated with postsecondary enrollment and degree attainment and whether the timing of the certification influenced that relationship. Earning a certification in high school prepared students for success in both 2 and 4-year colleges. However, the patterns of certifications and college enrollment and degree attainment differed based on when students earned the certification. For early earners the certification was more of a pathway to 4-year college; for later earners, the certification was a pathway to 2-year college.