In postsecondary education, technology and online resources have become a pervasive component of learning, but they are not always accessible. For students with intellectual disabilities, completing technology-dependent tasks may pose unique challenges that are not always addressed by the disability support services offered at the university level. During our fieldwork, we have observed several barriers to online education tools in a postsecondary environment for students with intellectual disabilities. For example, a student with an intellectual disability submitting an assignment via email to an instructor may encounter difficulties recalling and navigating to the location of their attachment file. In this paper, we describe core skills and common interfaces that we have identified as problematic for this population through an emic ethnography. We offer emic (perceptions from within a given environment) experience accounts to highlight the obstacles we have observed in a) information retrieval, b) navigation and information architecture c) file management, and d) password management. As researchers and educators involved in a postsecondary program for young adults with intellectual disability (ID), we have spent considerable time working with this population. For each scenario, we offer examples from our own experience of the techniques and technologies that did or did not help students accomplish these tasks. Based on these experiences, we provide recommendations for mitigating these barriers including education and training for students and developers and the use of existing interventions and tools. We also discuss future directions for this work. We believe that heightened awareness and communication between educators, designers, and students with disabilities will help address these problems and generate solutions which provide more accessible education experiences for learners with diverse needs.