While Latina/o enrollments in higher education are on the rise, more than half of these students enroll at a unique institutional type, Hispanic-Serving Institutions (HSIs). As Latina/o enrollments in higher education increase, the number of HSIs and emerging HSIs also increases. Knowledge is presently limited on the Latina/o college choice to enroll at these institutional contexts and subsequent educational outcomes. This two-part study sought to address the gaps in research on Latina/os' college choice process and educational outcomes at these institutional types. Data were taken from the Higher Education Research Institute (HERI), Cooperative Institutional Research Program for the 2004 freshman and 2008 senior survey. Critical race theory and community cultural wealth (Yosso, 2005) in conjunction with the Multi-Contextual Model of Diverse Learning Environments (Hurtado, Alvarez, Guillermo-Wann, Cuellar, & Arellano, 2012) informed the conceptual model guiding this study. Multinomial logistic regression was employed to understand how different forms of capital influence Latina/os' decisions (25, 916 freshmen) to enroll at HSIs (21), emerging HSIs (23), and non-HSIs (519). Multiple regression analyses were also conducted to understand how background characteristics and capitals and student experiences across these three institutional contexts influence two outcomes representing empowerment, academic self-concept and social agency. This longitudinal component of the study examined 2,123 Latina/os across 249 colleges and universities, of which 18 were HSIs and 14 emerging HSIs. Results indicate that there are notable differences on background characteristics and capitals that are clearly tied to enrollment decisions at these three institutional contexts. In general, the findings provide evidence regarding the positive influence of familial capital for Latina/os at HSIs, resistant capital for Latina/os at non-HSIs, while also further supporting the importance of more previously researched forms of capital, namely cultural, human, and economic. With regards to change on academic self-concept and social agency between college entry and four years later, there were differences contingent based on the institutional context. Gains on academic self-concept were the largest for Latina/os at HSIs while the gains were essentially equal on social agency across the three institutional contexts. Further, there were distinctions between predictors for academic self-concept and social agency across the three institutional types, which indicate that these contexts matter when assessing Latina/o student experiences and eventual outcomes in higher education. These findings advance the notion of disaggregation by institutional context as essential in understanding Latina/o students' experiences and outcomes in higher education. [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.]