Special program and other school administrators regularly confront the issue of whether students under their charge are entitled to receive homebound instruction and if so, what procedures and criteria they should apply in coming to a proper decision. Where a student is entitled to such services the administrator must decide what subjects must be taught as well as their duration, intensity and frequency. Although virtually all state legislatures have addressed a student's right to receive homebound instruction the right to such benefits may intersect with those arising under federal laws such as the Individuals with Disabilities Education Act (IDEA/2004), the Rehabilitation Act (§ 504) and the Americans with Disabilities Act, thereby creating confusion for many administrators. In June, 2007 the Virginia Department of Education ("VDE") promulgated Instructional Services guidelines implementing the state's statutory requirements. Since the problems of homebound instruction school administrators face are substantially similar across jurisdictions the 2007 VDE guidelines provide an outstanding pedagogical vehicle for educational leadership and policy students in Virginia to practice making decisions about educational entitlements in a safe way. Moreover, it affords them an opportunity to develop analytical and interpretive skills which are transferable to other contexts. It also affords the students an opportunity to consider how local policies are developed and the importance of including the right stakeholders in that process. The author has designed a series of fact patterns where students are asked to apply the VDE guidelines to those patterns. The patterns and their questions can easily be adapted to fit the requirements of other state jurisdictions.