When K-12 school districts began implementing the first student information systems (SISs) during the 1990s, special education was largely left out of the process. The two systems evolved as separate entities, technologically speaking, and in the handling of individualized education programs (IEPs), paper remained the dominant storage medium long after other student records had made the digital transition. An IEP is a written document developed for an individual public school student who qualifies for special education. These documents are highly customized, team-developed, narrative in nature, annually reviewed, and subject to federal and state scrutiny. On the other hand, much of the student data needed to make special education determination resides in the SIS: grades, attendance records, test scores, discipline information. If a district's IEP structure does not display this information easily, IEP planners have to navigate across two systems, fostering errors and discouraging usage. This article discusses challenges of integrating these two systems and reports some of the efforts made by several school districts to do so.