Students with disabilities have diverse needs that can be difficult for schools to meet. One promising approach that addresses this issue is Linked Learning, a high school reform initiative aimed at simultaneously preparing all students for college and career (ConnectEd, n.d.). Although research has shown that participation in Linked Learning is associated with positive student outcomes such as higher rates of graduation and enrollment in postsecondary institutions, educators continue to report difficulties of Linked Learning schools to meet the needs of students with disabilities (Guha et al., 2014; Saunders, Rogers, & Terriquez, 2013). Significant inconsistencies in the implementation of Linked Learning practices across districts may be impeding the initiative's equitable and meaningful impact for all students (Saunders, Rogers, et al., 2013). Likewise, the fragmented nature of special education service delivery related to transition programming has historically disrupted the achievement and sustainability of positive outcomes for students with disabilities. This convergent mixed-methods study compared transition practices in both Linked Learning and Non-Linked Learning high schools, examined the self-determination, career maturity, and school engagement of students from both settings, and investigated the factors that inhibit or facilitate effective transition programming. The quantitative phase consisted of a cross-sectional survey design and the qualitative phase included individual semi-structured interviews. Participants included a convenience sampling of special education teachers and students with disabilities from six Linked Learning high school districts and six non-Linked Learning high school districts in the Central Valley region of California. Findings suggest suboptimal levels of implementation fidelity of overall transition programming across schools. Nonetheless, compared to Non-Linked Learning teachers, Linked Learning teachers reported higher levels of implementation of specific transition practices related to students' self-determination and career maturity and teachers' professional development. Interaction effects were found between grade level and Linked Learning pathway participation on student behaviors related to career maturity. The findings also suggest areas for developing practices and future policy initiatives relevant to transition programming for students with and without disabilities. [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.]