Students with disabilities (SWDs) require a transition process to support high school graduation and continuation to higher education or the workforce. In a rural district in a southern state, the problem investigated was only 37% of SWDs were graduating from high schools in the target district, compared to 79.9% of students without disabilities, which suggested that the transition design and implementation did not support SWDs' needs. Using a transition-focused conceptual framework, the purpose of this basic qualitative study was to understand the perceptions of educators regarding the design and implementation of the transition process for SWDs at the high schools in the target district. The perceptions of general and special educators about the strengths of and barriers to the transition process were investigated through interviews with purposefully sampled participants from the target district. Six participants were general educators and special educators, including central office leaders who were experienced with the transition process for SWDs. Inductive analysis revealed patterns and themes including collaboration, systemic assessment, parent resistance, and a need for a more functional curriculum for SWDs. A white paper was developed to inform district stakeholders of the findings and offer recommendations for bolstering the transition planning process in the district. Implications for positive social change include strengthening strategic transition planning to better prepare SWDs for postsecondary outcomes by incorporating instructional content for transition in social, academic, independent living and employability skills which may result in increased independence as well as improved communication and coordination with parents and other relevant stakeholders. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]