While there has been some research detailing the difficulties that special educators have with compiling the complex paperwork required by the federal Individuals with Disabilities Education Act (IDEA) mandate, little has been written about how technology weighs into this framework, or how teachers use data to assist with their instructional planning. This study explores in what ways, and to what extent, one special education technology system, EasyIEP(TM), impacted the work of special education teachers in the School District of Philadelphia (SDP). Through a mixed-methods approach, consisting of interviews with principals and special education teachers and surveys administered to special education teachers, this study documents the experiences that teachers had as they infused EasyIEP(TM) into their daily work and came to understand special education through its lens. The findings of this study serve to: 1) document the benefits and flaws of the web-based tool as it relates to special education teachers' work; 2) describe the extent to which special education teachers' instructional, procedural and regulatory, and data informed practices were informed by their use of EasyIEP(TM); and 3) demonstrate how EasyIEP(TM) guided conversations among teacher groups and administrators, contributing to a more knowledgeable and inclusive school community. The divergent experiences of low incidence and high incidence special education teachers in this context were also explored. Further, this research offers a complex, multi-faceted understanding of how one web-based system works in context in a large urban district and offers a detailed account of the challenges facing special educators, from legal compliance, to instructional planning, to data informed discussions and inclusive practices, as seen through the analysis of a practitioner/researcher. The implications and recommendations for schools interest in implementing web-based systems included: offering consultation and training to district and training special educators and other school leaders on data, technology, and special education practices. [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/en-US/products/dissertations/individuals.shtml.]