At the first and only public Montessori charter school in New York City, teachers create learning environments, materials, and lessons that help students guide themselves to find information needed to arrive at a necessary learning outcome. The sudden shift to online instruction in March 2020 required parents, teachers, and administration to maintain business-as-usual in an unfamiliar modality--online instruction. This case study reflection article focuses on the planning strategies identified and implemented that shifted the school to teaching and learning online during the COVID-19 pandemic while working to keep the Montessori philosophy alive, despite the expansion to the online modality. Existing research, the process of shifting to the online modality, maintenance of the Montessori approach, and the inter-institutional support provided to the charter school by a community college are reviewed. Once mandated to move to online instruction, strategies employed show that maintaining students' natural desire to learn and active discovery are central objectives in tandem with supporting the relationship-centered culture in the machine-oriented online-learning environment. This dual focus is critical because children's development is maximized when they are engaged in secure, mutually collegial relationships (Greenfield & Suzuki, 1998). It was concluded that building community among children and teachers, as well as between administration, teachers, families, and a partnering community college were valued and deemed critical to sustaining the rigorous curriculum and relationship-based school culture during the pandemic crisis.