This dissertation disaggregates the "Hispanic" category to examine the various factors shaping the educational trajectories of students who encompass this large ethnic group. This project consists of three studies, each presenting the perspectives of principal stakeholders: families, schools, and a community-based educational initiative. All studies are situated in the high-poverty and racially/ethnically-segregated school district of New Riviera, NJ (pseudonym), whose Hispanic student body increased from 51 percent in 1999 to 90 percent in 2019. The first study explores the experiences of "low-income, Hispanic" parents navigating the U.S. school system. I draw on data from forty parent interviews and employ qualitative methods to discern the sociocultural components shaping the families' relationship with the schools. Findings indicate that the factors allowing some families to forge resourceful relationships and to garner cultural values rewarded in schools -- factors that ultimately facilitate their negotiation and navigation of the schooling system -- include: higher than average income levels, higher rates of full-time employment and exposure to professionals, higher levels of education, integration to communities outside the local district, permanent legal status, long-term plans to reside in the U.S., immigrating from an urban area (as opposed to rural), and an understanding of education that aligns with U.S. values. The structure of the school system benefited those families possessing the involvement strategies and the cultural and social resources that resemble those of dominant groups; thus, parents who adopted a U.S.-centric approach to their school involvement, negotiated their role in the schools with ease. The second study examines how New Riviera schools responded to the major demographic change in the student body and how they support their diverse Hispanic student population. I combine three sources of data and use qualitative and quantitative methods to analyze the district's policies and organizational structures, as well as the attitudes and practices of individual educators. The data sources include district records and periodicals dating from 1970 to 2019, interviews with current and former district staff, and a staff-level panel dataset. Findings suggest that the rise in Hispanic student population in New Riviera was accompanied by a diversification in terms of: country of origin, socioeconomic status, immigration status, home language, schooling histories, and parental level of education. In concrete terms, this occurrence manifested in variations in students' access to academic and non-academic resources, access to higher education opportunities, time availability and predisposition to engage in academic activities outside of school, and parents' ability to get involved in their children's education. Most policies and practices adopted by the district over the past decades to support their growing Hispanic population were generic and disjointed, failing to fulfill the community's demands and to recognize and support students' diverse needs. Findings also reveal that a deficit discourse permeates the internal order and social relations within the schools; the context set out by the district that is marked by low student expectations and teacher demoralization appears to hinder collective responsibility for student learning. Despite this, educators who possess a profound understanding of their students' lives and cultural backgrounds function with a certain degree of autonomy that allows them to engage in culturally responsive teaching. The third study focuses on an after-school and summer program located in New Riviera to understand how a community-based initiative adapts to the varying needs of its majority-Hispanic student population. This work also examines the initiative's effects on social capital development and on students' academic performance. I employ a mixed-method approach using program records, a student-level panel dataset, student focus groups, and program personnel interviews. Findings suggests that program personnel recognize the cultural and circumstantial diversity present in their student population and respond to students' differing needs by implementing various purposeful, culturally-sensitive practices, such as allowing students to bring their siblings to program sessions and fostering trusting relationships with parents. The program's organizational structure, particularly its collaboration with locally based organizations and institutions, strengthen its capacity to extend students' social networks and facilitate the formation of life-enhancing bonds. From an academic standpoint, the results from this dissertation demonstrate that the treatment of Hispanics as a homogeneous population obscures the reality of diverse educational paths: shared ethnicity does not manifest in a monolithic experience, as a host of social, economic, political, and cultural in- and out-of-school factors affect students' trajectories. From a policy standpoint, this project sheds light on the differing needs of students comprising the "Hispanic" group and shows that schools need to increase their efforts to learn about the realities of their students' lives, and adopt context-dependent and culturally-sensitive practices to connect with students and parents. At the same time, this work recognizes that schools do not operate in a vacuum, and that factors affecting Hispanic students' schooling trajectories transcend education policy and reflect larger, structural societal problems. [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.]