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Research studies have documented differences between first-generation and continuing generation students’ pre-college expectations and experiences once enrolled. Beyond stating that differences exist, most do not explore whether or how these expectations are aligned with actual college experiences. This study explores how first-generation and continuing generation students’ educational experiences align with their expectations while they are enrolled in college. Interviews with students attending a public research university suggest there is a misalignment in the expectations students have surrounding their academics, college costs and their community of support in college. Understanding how students’ experiences align with their expectations can help scholars and practitioners cultivate specific learning opportunities that will help first-generation and continuing generation students achieve their educational goals.