Although fostering self-determination has emerged as a central element of recommended and evidence-based transition practices for adolescents with disabilities, few studies have examined the paths through which students develop the skills and dispositions that can enhance their self-determination and successful transitions. The authors used path analyses to examine the ways in which exposure to quality secondary learning environments contributed to the development of self-efficacy, motivation, and academic achievement among 135 high school students receiving special education services. Students with disabilities who reported having greater involvement in learning environments reflecting recommended transition practices (i.e., high-quality learning environments) demonstrated increased career-search self-efficacy. Students with greater career-search self-efficacy were more highly engaged in goal setting, which further predicted their motivation to attend school and academic self-efficacy. Finally, students with higher academic self-efficacy were found to have higher grades. The authors offer recommendations for enhancing the self-determination skills and opportunities of youth with disabilities by strengthening the quality and impact of transition education.