Efforts to promote self-determination have been a principal focus of transition planning in support of students with disabilities for nearly two decades. However, research and recommendations related to self-determination have been primarily centered on promoting student participation in the IEP process and ensuring broader preparation for effective transition planning in the later school years. Beyond fruitful participation in the IEP process itself, students with disabilities who are included in general education settings require self-advocacy and communication skills in order to ensure the effective and consistent delivery of their designated IEP accommodations, which are designed to facilitate their successful acquisition of academic content and overall learning. This article describes a model for teachers to employ when training students with disabilities to self-advocate on a day-to-day basis, thereby supporting students' ability to obtain needed accommodations while also engaging school contexts with a positive sense of self-directedness, agency, and efficacy. (Contains 5 figures.)