Pedagogical practices in singing need to be responsive to the challenges and leverage the affordances of engaging young singers, growing up in today’s fluid and fast-changing digital age, in deep, meaningful, and enduring learning of western music and singing traditions. Little is known about the extent to which singing engagement fosters transformative experiences and very little empirical research has examined potential factors leading to engagement in transformative singing experiences. This research draws on transformative music engagement (TME) as a perspective for understanding and developing transformative pedagogical approaches in choral music education. Theory and practice are interrelated and examined in relation to the transformative paradigm through (1) case study interviews with choral singing leaders from four countries (Cuba, Kenya, Ukraine, Denmark) using ethnographic encounters and narrative inquiry to identify key attributes of transformative singing leadership (TSL), and (2) an action research study involving an interrelated 16-week program development component and study using an innovative retrospective assessment procedure to examine 50 secondary school students’ perceptions of transformative singing engagement (TSE) involving two singing capacities (embodied physicality and communicative expression) and three learning capacities (engaged agency, connectivity, and values/self-beliefs). In the case studies involving ethnographic encounters, four main attributes of singing leadership emerged: (1) developing skill and expression, (2) fostering resiliency, (3) forming cultural singing identities and intersectionalities, and (4) promoting social innovation. Findings from the TSE study with secondary school students showed positive conceptual shifts in students’ perceptions across all comparison variables. The findings also suggest the importance of integrating across singing and learning capacities for TSE to enable students to engage in personal meaning making in and through singing. This research identifies key affordances of transformative singing leadership and transformative singing engagement, which can assist both learners and leaders of singing in creating deep, meaningful, and enduring learning opportunities.