This article examines the link between secondary school context and both college completion and timely college completion. A quantitative methodology is applied to study the cohort of Chilean students who began postsecondary studies in 2008. Specifically, multilevel logistic regression models were considered. The results show that students who graduate from public secondary schools, who follow vocational educational tracks, who take more time to enroll in college after finishing secondary school, and who do not receive financial support have lower odds of completing their college degrees. As far as timely college completion is concerned, this study shows that students who graduate from private schools and rural schools and who receive financial support have higher odds of completing their studies in a timely fashion. Policy implications to support students who find it more difficult to succeed in higher educational contexts are discussed.