Although previous research provides empirical support for the Freshman Myth, qualitative inquiry is necessary to enhance our understanding of the content, complexities, and impact of students expectations about college. The current study analyzes in-depth interview data from nine students at three key time points in their transition from high school to college to provide new insights into the nature of students expectations about college, their subsequent first-year experiences, and how expectation fulfillment or disillusionment affects students adjustment to college. Findings revealed two new areas of student expectations about college: interpersonal relationships and personal development. Further, while their personal and interpersonal experiences in college resulted in some expectation disillusionment, most notably with respect to roommates, students generally felt well adjusted and that their first-year experiences lived up to their expectations. Specifically, their relationships with their families, exposure to new people and ideas, pursuit of personally and professionally relevant coursework, and progress toward their goals for individual development all met or exceeded their precollege expectations. The practical, methodological, and theoretical implications of these results are discussed, which help broaden our current understanding of student expectations about college, provide meaningful feedback to faculty and staff at the high school and college levels, and inform future research in this area.