The COVID-19 pandemic has been one of the most dramatic and far-reaching events to impact education in recent years. At the onset of this global crisis, schools were required to pivot, with little warning or planning, to educate the more than 50 million school-age children in the United States through some form of nontraditional instruction (NTI), which often involved technology-based distance education. While shifts to NTI for short time periods may be feasible for many students, the potential impact of long-term NTI on students with extensive support needs (ESNs) and their families, especially in rural areas, may be particularly acute. In this article, we discuss specific strategies that address and incorporate what we know about extended NTI in rural school districts, including both lessons learned and areas of concern, with particular attention to the role and importance of caregivers. We outline ways that caregivers can be supported and how natural environment teaching provides one useful framework for efforts to reduce skill regression and to increase the overall potential for skill generalization when traditional schooling is interrupted.