This quantitative study aimed to expand upon existing research, which discussed student expectations, the relationship between expectations and retention, persistence, and student success, as well as why understanding student expectations is important to supporting student success. This research study explored these concepts from a lens of Generational Theory, which includes the notion that each generation has differing values, experiences of life events and motivational factors. Effective delivery of services, which can aid student success and retention, is enhanced when professionals within student affairs are able to appreciate students as individuals, as well as who they are as a generational cohort. Each generational cohort of students brings its own unique perspective to campus, and it is important that thinking and practices of higher education leaders shift to meet the changing expectations of students. Data in this study were gathered from an online survey administered at five colleges and universities with the State University of New York System in the United States, during the fall 2021 semester. The participants in this study were undergraduate students enrolled in either a 2 or 4-year degree program and were aged 18-26, which at the time of the study identified them as Generation Z college students. The specific areas within student affairs of interest to this study were: (1) student leadership, engagement, and/or activities on campus, (2) health and/or counseling departments, and (3) college housing/residence life. Findings included identification of multiple factors with statistically significant associations with services most expected from these areas within student affairs, associations with preference for how services are delivered, and whether expectations were met when services were utilized. Two of these factors were Generation Z generational characteristics, a preference for face-to-face interactions and the importance of technology in daily life. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]