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Increasing the rigor of courses taken in high school is a crucial part of education policy. However, existing knowledge about high school coursework is outdated. Using data from a recent nationally representative data set, this brief reports results that expand our knowledge base on the relationship between rigorous coursework and postsecondary outcomes. Findings show that (1) Timing of the course-taking matters; (2) Advanced coursework is important; (3) Students who take diverse courses are likely to have better postsecondary outcomes; and (4) Both the quality and quantity of the coursework matters. The results of this study have implications for students, parents, educators, policymakers, and researchers. Students and their parents who would like to increase students' chances of becoming successful after high school should ensure students do not fall behind in taking the specific courses outlined in this study and enroll in advanced courses after completing the prerequisites for those courses.