Post-secondary education has been deemed the segway to lifelong opportunities for students graduating from high school including heightened career paths, increased occupational earnings and overall life satisfaction. The implications for successful post-secondary education are intensified for students with learning disabilities (SLD). While the numbers of students with disabilities enrolling in higher education continues to rise, the ability of those students to keep pace with that of their non-disabled peers is declining. Effective transition planning may increase student success and diminish the risk of students falling behind, especially students with learning disabilities. The purpose of this study was to understand, through a qualitative phenomenological design, the perceptions of K-12 special education professionals and higher education administrators on the successful transition of students with learning disabilities to college. Sources of data included responses from eight participants, selected via purposive and convenience sampling, to open ended questions which were conducted during semi-structured video conferenced interviews. Three themes emerged from this study: under prepared, college expectations versus high school experiences, and self-advocacy. [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.]