This chapter describes the use of a family of Electronic Performance Support Systems (EPSS) to support teachers and students with mild disabilities, especially those with special learning and behavioral needs. This approach uses technology to support students in educational environments. In this chapter, the authors provide a brief overview of the family of tools and describe the need, rationale, and technical development process of the latest tools in the family, PictureTools™ and PictureTools-Mobile™. These tools are designed to support positive behaviors of young children, incorporate both images and video, and in the case of PT-Mobile, the capacity to run on iPod and iPad. In addition, they report the results from two federally funded projects related to development, usability, and feasibility testing of these tools. Future research directions are discussed.