In the past decade, digital media usage has exploded. With the shifts in availability of personal technology, educational practice must also shift. Digital media through the context of a universally designed learning environment can be utilized to promote and honor the multiple identities and repertoires of youth with disabilities. If the goal of education is learning, then it is imperative to ensure that all tools are geared toward removing barriers to learning. When there is a mismatch between the learner and the environment, learning is improbable and, in some cases, impossible. Three common areas of mismatch are cultural, environmental, and emotional mismatches. Digital media tools, even with the criticism of newly emerging tools, like AI, give access and affirmation to learners while providing opportunities for codesigning a match for learning. The future implications of digital media on educational strategies for disabled youth that promote, honor, and include their multiple identities and repertoires in special education and beyond are multifaceted and depend on how designers of the learning experience view the barriers and eliminate them. Eliminating barriers requires moving from “designing for” to “designing with.”