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The authors examine students’ linear progression histories in mathematics throughout high school years, using the High School Longitudinal Study of 2009. Although scholars have attended to this before, the authors provide a new organizing framework for thousands of heterogenous mathematics course-taking sequences. Using cluster analysis, the authors identify eight distinctive course-taking sequence typologies. Approximately 45 percent of students take a linear sequence of mathematics, whereas others stop taking mathematics altogether, repeat coursework, or regress to lower level courses. Only about 14 percent of students take the expected four-year linear sequence of Algebra 1–Geometry–Algebra II–Advanced Mathematics. Membership into different typologies is related to student characteristics and school settings (e.g., race, socioeconomic status, and high school graduation requirements). The results provide a tool for schools’ self-assessment of mathematics course-taking histories among students, creating intervention opportunities and a foundation for future research on advancing our understanding of stratification in math course-taking patterns, postsecondary access, and science, technology, engineering, and mathematics majors.