In March 2020, COVID-19 appeared in the State of Maryland, resulting in strict stay-at-home orders and the shutting down of physical business operations. These restrictions directly impacted College Park Academy (CPA), a public charter middle and high school in Prince George's County, MD that typically follows a hybrid approach to in-person and online instruction. The purpose of this qualitative study was to review CPA's transition to full online distance learning during emergency remote teaching. The research worked to establish a snapshot of the school's underlying structure and disaster preparedness strategies before evaluating the perceived viability of the online model and its effects on students, teachers, parents, and educational administrators. The researchers conducted interviews, as well as document analysis and online classroom observations. The findings reveal that despite strong infrastructure and communications during the transition, there remained issues with school readiness, including the maintenance of academic rigor and social emotional wellbeing. Overall, recommendations are made as to how the school would benefit from a shift in its approach to technology-enhanced learning, including the need for digital tools that better facilitate wellness checks, provide human touchpoints, and target collaborative, student-centered pedagogy. These lessons learned are relevant for other school administrators to consider as society continues to adapt to a new era of virtual learning during times of crisis.