How do college students select courses? The question is important because course selection is directly implicated in commitment to major and timely completion, yet social scientists have remarkably little empirical knowledge of how course selection occurs “in the wild” of everyday undergraduate life. Our work fills this gap by leveraging data from a longitudinal study of undergraduates considering and selecting courses at Stanford University from their initial entry in 2019 through to graduation. We find that course selection is complex and contingent, in five ways. First, students confront many more curricular offerings than they can reasonably expect to be aware of, let alone comprehend. Second, salient aspects of any course are endogenous: each option represents a bundled choice of content, instructor, grading regime, workload, and meeting time. Third, students have virtually no control over curricular offerings, such that each selection is a tradeoff. Fourth, academic coursework is only one component of personal utility, which often also includes multiple extracurriculars with serious time demands. Fifth, personal utility is often dynamic, changing over time as college experiences unfold. Findings overall encourage scholars and practitioners of undergraduate academic progress to attend directly to the organizational conditions of course selection.