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Indigenous communities located in remote areas have experienced extreme socioeconomic stress. School leaders serving these communities face unique challenges. The Covid-19 pandemic has placed further major obstacles to the delivery of education in the communities during school closures and emergency remote teaching (ERT). The paper reports on a case study investigating four principals’ experiences during the pandemic in a remote, fly-in Indigenous community in Northern Ontario. Principals pointed out that limited technology access and skill-training coupled with an array of complex factors resulted in disengagement and a loss of learning for many Indigenous students despite the schools’ concerted efforts. Suggestions were made to tackle systemic challenges, including increasing Indigenous representation in educational leadership and integrating culturally responsive pedagogy.