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There has long been a call for democratic practice in education. Unfortunately, current times seem to be trending more toward one-sided dogma (e.g., book banning, whitewashing history, outlawing CRT and discussion of diversity, inclusion, and equity) rather than toward democratic inquiry, discourse, and practice. Nevertheless, outlier schools to current conservative and repressive norms do exist—schools that function democratically and progressively. In this qualitative case study we focus on one such school to see what can be learned from its history, practices, and efforts at sustainability. From the case school’s experience, we identify some of the problematic issues of democratic schools and discuss how other schools might learn from our case school’s experiences.