The purpose of this research is to unpack and learn from the experiences of teachers who deliver courses to remote secondary school students by videoconference. School districts are using videoconferencing to connect students and teachers who are separated geographically through regular live, real‐time conferences. Previous studies have shown the inadequacy of videoconferencing to create effective learning communities when used solely as a lecturing tool, but there is limited research into understanding how to mitigate the challenges in order to leverage the tool for what it affords. This collective case study uses qualitative methods to examine those challenges and propose strategies for overcoming them. Five obstacles were identified (insufficient time, feelings of isolation, scheduling and logistics, unreliable technology and limited personal connection) with the following recommendations: leverage supporting tools, intentionally build presence and prioritize the programming within the district.