This study uses data from 15 descriptive case studies to explore high school students’ perceptions of scholarships and the forces that contribute to these perceptions. The findings describe six themes that emerged from the data analyses: (a) awareness of scholarships; (b) perceptions of institutional scholarships; (c) motivations for pursuing scholarships; (d) barriers to pursuing scholarships; (e) sources of information about scholarships; and (f) potential strategies for encouraging more students to pursue scholarships. The article concludes by identifying implications for policy, practice, and future research.