This dissertation consists of three empirical studies that explore the educational experiences and trajectories of English learners (ELs) and students with disabilities. The first study uses longitudinal data from four large California school districts to examine the characteristics of long-term ELs (LTELs) and former ELs—those reclassified as English language proficient—with Learning Disabilities (LDs) and to explore high school absenteeism within these groups. The results indicate that LTELs and former ELs exhibit lower absenteeism rates than their non-EL peers. However, LTELs with LDs experience higher absenteeism rates than former ELs with LDs, particularly in the upper grades of high school. The second study explores heterogeneity in career and technical education (CTE) coursetaking across 16 career clusters and the associated outcomes for LTELs, former ELs, and non-ELs. Using the Texas Statewide Longitudinal Data, this study examines whether CTE concentration in high school is related to the completion of postsecondary credentials and workforce earnings and explores variation among non-college-going students. The findings reveal a nuanced effect of CTE concentration: across all groups, irrespective of postsecondary participation, health science and STEM clusters enhance credential attainment and earnings, with the manufacturing cluster yielding the highest labor market returns. While former ELs and non-ELs similarly benefit from CTE concentration across clusters, LTELs do not equally share these benefits. The third study leverages the Texas Statewide Longitudinal Data to examine the characteristics of students with non-apparent disabilities who receive disability accommodations in community college, including those with LD, other health impairments (OHI), emotional and behavioral disorders (EBD), and autism spectrum disorder (ASD). This study examines whether receiving accommodations and the timing of their initial receipt influence degree completion and vertical transfer. Findings reveal that students with LD and OHI consistently benefit from accommodations, regardless of when these supports are accessed. However, students with EBD and ASD do not uniformly benefit from accommodations; notably, students with ASD who delay accommodation requests until their fourth semester or later are less likely to complete a degree or transfer.