As the number of students with disabilities pursuing postsecondary opportunities continues to grow, along with an increase in digital educational content and technology, the issue of digital accessibility becomes increasingly urgent - both as a matter of equity and access for disabled students and as a matter of social and fiscal responsibility for postsecondary institutions. When postsecondary institutions fail to meet the requirements of disability legislation, the U.S. Department of Education's Office for Civil Rights (OCR) is the federal entity responsible for enforcement and complaint investigations, handling hundreds of complaints related to digital accessibility at postsecondary institutions since 2013. There are significant gaps in the existing literature on how to get from the technical requirements of digital accessibility to the actual implementation of accessible content in systems as complex as postsecondary institutions. This qualitative study uses a single case study methodology, leveraging manifest content analysis and coding processes, to analyze 37 formal complaint investigations, findings, and resolutions agreements, filed from 2018 to the present, related to digital accessibility at public, post-secondary institutions. Study results indicate that digital accessibility conflicts persist primarily due to the complexity of the problem, the complexity of the stakeholders and institutional dynamics, and the complexity of the technical work required to remediate inaccessibility content. The results of this qualitative study are intended to assist postsecondary institutions in better serving their students with disabilities by shifting their digital accessibility approach from reactive to proactive. [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.]