In this article, a measure of students’ beliefs is constructed from three sources of information on 12,509 high school seniors from the Education Longitudinal Study (2002 to 2006). First, verbatim responses to questions on occupational plans, drawn from restricted-access data records, are coded into 1,220 categories to capture detailed information (specific job titles), extended information (the listing of multiple jobs), and contradictory information (the listing of multiple jobs with divergent characteristics). Second, the educational requirements of detailed jobs, as specified in the U.S. Department of Labor’s Occupational Information Network database, are matched to all jobs that students list within their verbatim occupational plans. Third, student perceptions of the educational requirements of their planned jobs, which were revealed in response to a follow-up question posed immediately after they provided their verbatim occupational plans, are used to identify students with puzzling beliefs about their educational and occupational trajectories. The authors then show that (1) students who are categorized as having uncertain and/or inaccurate beliefs about the educational requirements of their expected jobs have lower rates of college entry than those with certain and accurate beliefs, and (2) among entrants, these same students have lower rates of immediate college enrollment and lower attendance at four-year colleges.