COVID-19 has engendered serious challenges with the provision of special education services for youth and young adults incarcerated in U.S. adult correctional facilities. This article describes the recent lawsuit, Charles H. et al. v. District of Columbia et al., which focused on the lack of a free and appropriate public education (FAPE) at the Inspiring Youth Program (IYP) school in the Washington DC jail during the pandemic. Following a brief review of relevant components of the Individuals with Disabilities Education Act (2006) regulations, we describe the three areas in which there were violations to the provision of IDEA and FAPE, as well as the harm incurred. Specifically, we discuss the lack of: (a) instruction and monitoring of youth academic progress; (b) related services (i.e., behavioral interventions and supports, counseling); and (c) DC public schools Office of the State Superintendent of Education (OSSE) supervision and oversight. Finally, we provide a discussion of the need for compensatory education to remediate harm.