In collective free music improvisation (CFMI), performers draw on their unique skills, experiences, and musical backgrounds to create an evolving blend of musical sounds in response to real-time situations and stimulus. Collaboration emerges as players respond to each other’s real-time musical cues and intentions, engaging in a dynamic dialogue shaped by their existing competencies and socio-cultural influences. CFMI is thus understood primarily as a socio-communicative practice, offering music learners opportunities to strengthen social bonds, communication, and collaboration as they interact musically in the moment. These spontaneous exchanges encourage students to negotiate their differences through active listening and socially responsive playing. Such experiences closely align with 21st Century Competencies (21CC), including self and social awareness, relationship management, inventive thinking, and communication and collaboration skills. Yet, despite its educational value and contemporary relevance, CFMI remains underexplored and seldom practiced in formal school contexts. In response, an intervention research project was launched in Singapore to develop CFMI pedagogical strategies for primary and secondary schools. The study was conducted in two phases. Phase 1 comprised a three-session CFMI workshop for nine music teachers, which combined guided practice, pedagogical discussions, and focus groups to prepare teachers for CFMI curriculum design and delivery. In Phase 2, three teachers from Phase 1 implemented CFMI curricula in their school classrooms based on a pedagogical framework introduced during the workshop. This framework comprises three enablers: socio-musical interactions, personal musical vocabulary, and shared understanding (Author, 2018). These classroom implementations were examined as case studies. Data collected included classroom observations, teacher interviews, video recordings, and surveys of teachers and students, which were used to examine classroom implementation, learner responses, and the broader educational value of CFMI. Data was analyzed inductively using the constant comparative method, with case studies first examined individually and then compared to identify emergent themes. These themes were subsequently synthesized into overarching themes that contribute to an understanding of CFMI teaching and learning strategies. The findings suggest that, despite differences in curriculum design and delivery at the primary and secondary levels due to variations in student and teacher profiles, a key underlying enabler of CFMI is the use of authentic and/or relatable scenarios, narratives, and games as entry points into the socio-interactive play of sounds and silence that constitutes CFMI’s inherent network of communication. The findings also indicate potential alignment between the learning outcomes achieved through such socio-interactive play and 21CC.