An increasing portion of the U.S. population is interested in and enrolling in higher education, and colleges and universities across the country are responding and actively recruiting a wider variety of students than in the past to maintain if not increase enrollment (Holland 2015; Irlbeck et al. 2014). Many of these students are considered first-generation students--i.e., students for whom neither parent has earned a baccalaureate degree (Chen 2005; Irlbeck et al. 2014). For decades, these students have been relatively invisible in the higher education literature; however, scholars have begun to argue and highlight the ways that first-generation students encounter multiple obstacles in their collegiate journeys-- e.g., limited financial resources, few social connections and sometimes limited academic preparation, at least compared to their continuing-generation counterparts (Holland 2015; Perna 2015; Tabitha G. Wilbur and Roscigno 2016). In an effort to attain upward intergenerational mobility, many first-generation students enroll in college even when vulnerable to financial, social, and academic hardships. Education scholarship has examined these vulnerabilities and how they influence higher educational enrollment and retention (Holland 2015; Irlbeck et al. 2014; Perna 2015; Radunzel 2021; Rendon 1995) but analyses have mostly been limited to either elite higher education institutions or cross-sectional snapshots. This project builds on prior work, employs qualitative longitudinal data on first-generation students over time, and examines specifically how vulnerabilities may shift over the college years, how race and first-generation status intersect in meaningful ways, and the extent to which first-generation students experience some efficacy in higher education and relative to university resources and scholarship programming. My findings highlight some of the key vulnerabilities (i.e., lack of social integration, financial insecurity, and academic precarity) that first-generation students experience and how these vulnerabilities change over time. I also find that there are observable intersectional dynamics between a student's first-generation status, their race/ethnicity, and their educational experience. In particular, I find that first-generation students of color experienced the previously discussed vulnerabilities as well as difficult encounters with race-based discrimination during their earliest years. This often leaves them feeling even more isolated and insecure about whether they belonged at the University. Lastly, I find that first-generation students who capable of taking advantage of scholarship resources and programming are buffered to some degree them from some of the previously discussed vulnerabilities. Unfortunately, however, such resources and programming are not available to many. Overall, this project's results bring attention to the multiple and variable character of first-generation vulnerabilities in higher education, the influence of racialized experiences in higher education, and the importance of educational resources and sources of support. I also challenge future work exploring first-generation student experiences to: look beyond traditional examples of social belonging, especially when considering race and ethnicity; analyze more systematically the influence of academic scholarships on student well-being; and interrogate the role of supplemental resources that exist outside of the scholarship/award format. Along with addressing these points, my chapters shine a much warranted and general light on the heterogeneity of first-generation experiences over time. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]