For most experienced educators, choosing software for children with disabilities is challenging as the number of programs in our technology rich marketplace increases dramatically. Purchasing titles for entertainment is much less complicated than selecting effective educational materials based upon sound instructional objectives through a systematic review of characteristics of learner and learning environment. This study was designed to investigate the software selection process engaged in by special education teachers. Questionnaires were completed by 144 respondents with a return rate of 69% to (a) identify characteristics perceived as important to consider when determining which programs to select for use by students with high incidence disabilities, and (b) ascertain a list of software titles used in special education classrooms currently. Based upon qualitative data analysis, results indicated ten themes inservice teachers consider when selecting software titles. Those themes include: (a) welcoming; (b) sensory stimulating; (c) learner program design; (d) learner empowerment; (e) technology adaptation; (f) diversity; (g) individual instructional integration; (h) narration; (i) curriculum encompassing; and (j) teacher functionality. Additionally this paper provides a list of software titles used in classrooms currently and describes implications for integrating a software evaluation component into a methods course.