Transformative sustainability education has emerged as a vital approach for addressing the value crisis at the root of biodiversity loss, climate change, and socio-environmental injustices in the Anthropocene. Although schools are ideally positioned to drive this transformation, nature-based education often evaluates and targets individuals in isolation from their contexts. We examine how the spatial and social contexts of schools influence changes in human-nature relationships (HNR). We apply the same evaluative framework to two distinct educational settings: rural schools in Brazil, to investigate the contextualization of rural education within daily life, and urban forest preschools in Sweden, to investigate the ecological enablers surrounding meaningful nature-based activities. In Brazil, interviews with 32 students revealed that those students attending schools embedded in the local community developed a more profound, multifaceted, and more spiritual HNR, alongside a higher commitment to caring and advocating for nature conservation, compared with students in the conventional rural school. In Sweden, an analysis of 953 nature-based activities in three forest preschools indicated that the forests, trees, and diverse flora and fauna were the ecological catalysts for most mind-expanding, awe-inspiring, and overall meaningful nature experiences. Across both case studies, our analysis indicates that aligning pedagogical practices with the affordances and constraints of the surrounding social-ecological context is essential for encouraging shifts in HNR. Our findings underscore that the extent to which nature-based education can effectively be transformative depends on what the surrounding social-ecological context allows, promotes, or restricts. Therefore, embedding educational practices in their context and focusing on ensuring regenerative compatibility between educational activities and their local social-ecological system is central. Toward this goal, we further advance the BeNature framework; a transdisciplinary tool for designing and evaluating curricula in transformative sustainability education.