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In this qualitative, ecological, multi-site case study, we explore the work of four geographically and demographically diverse California Local Educational Authorities which have strategically leveraged recent state investments to pursue the twin goals of well-being and deep learning for adolescents. In this paper, we explore two interconnected cross-case insights: first, a promising pattern related to systemic investments in Career Technical Education, and second, a troubling pattern related to systemic stagnation in core academic courses. The findings from this study are intended to inform the work of district leaders, policymakers, and philanthropies, building a thickly textured and non-generic understanding of best practices with respect to using new funding sources and system levers to transform the experiences of adolescent learners.