The Individuals with Disabilities Education Act (IDEA) in 2004 outlined a series of mandates for special education teachers. Specifically, they must develop activities that promote skills to help their students become successful in adulthood. These activities became an additional requirement that needed to be navigated by special education staff, while they simultaneously had to ensure their students completed typical high school graduation requirements. Using sensemaking as my theoretical framework, in this paper I examine how groups of special education staff in four different districts navigate the constraints that exist within a typical high school, as well as developing transition skills to prepare students for adulthood. I provide an overview of the factors that impacted participants' sensemaking process and discuss ways to improve transition practices. Namely, exploring ways to help special education staff avoid isolation in this process and use their general education counterparts as resources. I provide an overview of the practices that can be embedded within the multi-tiered systems of support (MTSS) framework to accomplish this goal. In addition, using MTSS would circumvent other pitfalls that typically occur during the implementation of the transition mandate. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]