COVID-19 mitigation efforts resulted in many schools making the transition to online and remote instruction. Juvenile delinquents, as a group, attained lower academic achievement before the pandemic, and little was known how juvenile delinquents’ education fared after schools ceased face-to-face instruction. Using a mixed methods approach, three steps were conducted to analyze the education of juvenile delinquents in the United States: a qualitative literature review, a grounded theory study of teachers’ concerns in traditional schools, and an instrumental case study of juvenile delinquents’ enrollment during COVID-19. Researchers and experts recommended the development of a community online and in remote instruction, but most teachers felt overwhelmed and unable to rise to the challenge. Juvenile delinquents responded by most students disappearing from school attendance rolls. A grand theme, to shift the nature of online learning, is offered based upon the convergence of the research findings. A theory of humanistic schooling online, centered on a community of learners with the dimensions of academics, physical health, social, and attention to the individual, offers to radically transform practices and past recommendations.