Earning industry certifications helps people prepare for jobs in a range of careers. Doing so in high school may help students prepare for college as well. Using administrative data on two cohorts of first-time 9th graders in 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-year 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 closely associated with enrollment and attainment at 4-year colleges; for later earners, the certification was closely associated with enrollment and attainment in 2-year colleges. [This article was published in "Journal of Research in Technical Careers" (EJ1390740).]