The purpose of this IPA study was to understand how first-time, first-year traditional-aged residential students made sense of the transition experience at a small private residential college in the Boston area after participating in a 2-day overnight orientation program. Schlossberg's transition theory served as a theoretical framework for the study. Semistructured interviews were conducted with 10 rising sophomores at a small private, 4-year college in the Boston, Massachusetts area. The transcripts were carefully analyzed using interpretive phenomenological analysis. Four findings resulted from the analytic process: (a) orientation is a foundation for success; (b) orientation must meet student expectations and goals; (c) orientation affirms a student's enrollment decision; and (d) orientation influences persistence and retention. These findings emerged in the context of Schlossberg's transition theory and are positioned within the existing literature. Recommendations for practice include the need for small colleges and universities to (a) cohouse orientation and student activities to extend transition programs throughout the academic year; (b) provide information about campus culture before and during the orientation and transition processes; (c) provide access to tools and experiences for use during and after orientation, and (d) establish ways to understand and support student happiness and emotional well-being during the orientation and transition experiences. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]