In January 2020, a new state-wide art therapy in prisons program was established to bring art therapy to youth offenders in four prisons to help mitigate obstacles to their education, such as emotional dysregulation, behavioral issues, and cognitive difficulties. Shortly thereafter COVID-19 halted regular programming. In a system where sequestration is already a normative practice, over-isolation occurred. Art therapists developed strategies to continue providing services, including art-based workbooks and written correspondence. Three case vignettes and overall program feedback illustrate the participants' experiences and responses to the programmatic adjustments.