A small rural district in the eastern United States is experiencing challenges related to meeting the diverse behavioral needs of its special education students. After out-of-district placement options were limited due to the aftereffects of COVID-19, school leaders worked together to create a specialized program within their own district to meet the needs of some of their students requiring out-of-district placements. Although the local principal has a great deal of overall leadership experience, he finds himself ill-prepared to address situations involving discipline for students receiving special education services. The following case presents a principal thrust into a complex and unexpected situation that requires careful consideration of special education law, faculty support, and the rights of students with disabilities in the area of school discipline.