The rigid architectures inherent within formal schooling continue to influence young people's disengagement from education. Globally and locally, policy makers have proposed education reform and innovation, politicians have legislated for education change, yet still the problem of disengagement remains. This paper investigates one community's effort to support the reengagement in learning of young people aged 15-18 years in regional Australia through a flexible, online, community-based education program. Theoretically, this study used critical discourse as a way in to expose so as to explain dimensions of power and ideological positions as to what counts as learning. Critical ethnography as a methodology extended critical discourse's explanatory authority to a naming of spatial and social architectures and their impact on the young people's lives. Discourses of a braided curriculum, structural conviviality and emotional well-being were found to reduce some barriers to reengagement in learning; develop a shared, multi-disciplinary approach to reengagement; and be inclusive of young people's emotional well-being as central to the reengagement process. At this time of pandemic induced online learning as the new normal on a global scale, young people who are already vulnerable due to individual, school, and socio-cultural marginalising conditions deserve research processes with outcomes valorising their voices and those who work with them.