Very little research exists surrounding the systematic investigation of what steps are being taken to assist students with special education needs as they move from elementary to secondary school. These students often have greater difficulty with the transition, and this challenge is heightened even more for those using such specialized accommodations as assistive technology (AT) to support their learning. The purpose of this investigation was to determine current practices that help or hinder students using AT as they transition from elementary to secondary school. Four students, their parents, and their elementary and secondary school teachers in Ontario, Canada, were interviewed to determine current school practices that either, in their experiences, helped or hindered students using AT as they transition from elementary to secondary school. The participants' responses to interview questions were categorized into four themes: environment, assessment, training, and advocacy practices. The four themes that emerged in this investigation align closely with Blackhurst's (2005) discussion of primary concerns to be addressed when using technology with students who have learning disabilities. The authors present recommendations for a smoother transition. (Contains 1 table.) [This research was supported by the Dominion of Canada General Insurance Company.]