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This phenomenological case study explores how middle school teachers’ knowledge, skills, and beliefs about adolescent development, student engagement, and student voice shape their classroom practices. Drawing on in-depth interviews with teachers in a southern U.S. public school district, five themes emerged: legacy motivation, authentic alignment, collective thriving, navigating student voice, and professional learning as a bridge. Findings reveal that alignment between teacher identity and practice fosters student engagement and teacher well-being, while systemic barriers hinder implementation of developmentally appropriate instruction. The study highlights the importance of targeted professional learning and intentional support structures. Implications include reimagining middle school as a site for holistic development, where both students and teachers are empowered to thrive through relational, responsive, and equity-centered practices.