The COVID-19 pandemic forced the temporary closing of many brick and mortar school buildings in fall 2020 while substantially changing the delivery of instruction for students with and without disabilities in rural schools. This article describes the qualitative results of an online study completed between August 2020 and October 2020 that investigated rural educational leaders’ perceptions of the use of online instructional technologies before and during the COVID-19 pandemic. Rural educational leaders also shared how special education services were delivered and how parents felt about their children’s learning. The early school year in fall 2020 was a critical period for rural educational leaders as they were managing persistent and evolving issues related to providing quality educational opportunities to all students. This article provides a unique portrait of that crucial moment for educators, students, and parents.