Transition planning is an essential component of special education for students transitioning from high school to the adult world. The COVID-19 pandemic has impacted the ways in which transition education is implemented and has been a catalyst for change and potential improvement in transition education practices. Research is just beginning to emerge regarding the ways in which education has changed as a result of the pandemic. Teachers and transition coordinators are key stakeholders in the transition process and serve as a link between the school and the students and their families. Data was collected through semi-structured interviews with both special education teachers and transition coordinators from high schools in upstate New York. Interview questions addressed various aspects of transition planning and how this process has been affected by the COVID-19 pandemic. Responses were analyzed using the process of thematic analysis. Findings indicate that pandemic-related changes made it difficult to implement transition plans and made the role of the transition education provider more challenging. The Great Resignation had a profound influence on the transition process, resulting in staffing issues and changes in the employment landscape that impacted students transitioning out of high school. Increased use of technology played a major role, presenting both initial challenges and ongoing benefits for transition education. The impact of the pandemic on students and families was also a salient theme that played a role in transition planning and education. Study findings include various implications for the future of transition education. [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.]