This article describes a study of online educators' use of technology as part of the accommodations they provided to students with disabilities at their school. Specifically, research focused on four teachers who were members of an interdisciplinary team in a large virtual school program, in a state with established policies regarding online education, and online course work as a requirement for graduation. Data were collected over 4 months in a series of weekly interviews and through a content analysis of stipulated accommodations and modifications in student Individualized Education Program (IEP) documents. The findings of this study indicated (1) providing technologically grounded accommodations and modifications required intensive collaboration with students, parents, and other special education support staff at the virtual school, (2) online teachers struggled to keep up with all of the possible means and methods of enhancing the learning experience and providing accommodations that were stipulated in the IEP while also remaining sensitive to practices and supports that they could provide (using technology that were not mandated), and as a result (3) technology use as part of accommodation was most often relegated to what naturally exists in an online learning environment and is available to all students. The implications of this work are that transferring disability service plans, and IEPs in particular, is no simple matter, and that moving to a technological environment (and the notion that the online environment is inherently accommodating) needs interrogation at every level (practice, research, and policy).