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The phenomenon of the growing number of virtual schools engenders new conditions for teaching and learning. It is thus imperative to better understand these conditions and their impact on effective teaching and learning. This paper explores teachers’ experiences of a virtual high school through analyses of qualitative and quantitative data, which include ongoing communications with teachers from the virtual high school, an end-of-year summary meeting, and a 55-item questionnaire. Data analyses yielded several insights that pertain to pedagogical principles in the context of a virtual high school and that include personalized teacher-student relationships, new teaching skills, and emerging pedagogical, administrative, and technological challenges. Implications for providing potentially better conditions for learning in virtual contexts are discussed.