This chapter explores the idea of pedagogy as an iterative, evolving improvisation. We discuss two creative project case studies in the context of long-term care where residents were given the opportunity to explore collaborative improvisation and storytelling through music, using the Soundbeam, a motion-detecting musical instrument, along with iPads and traditional percussion. Although there is a growing body of literature on the benefits of creative music-making during later life (Creech et al., 2013; Creech et al., 2014; see Chapter 5 of this volume), particularly with regard to the social and cognitive benefits, there is significantly less research that examines the pedagogical approaches that can support creative and engaged music-making among residents in long-term care, especially from the perspective of the practitioner. Accordingly, this chapter discusses pedagogy as improvisational performance (Costa & Creech, 2019; Sawyer, 2004; Taylor & Francis, 2019), exploring the implications of a flexible and reflective facilitator paradigm that reconciles planning and structure with the need for in-the-moment flexibility informed by reflection-in-action. In this same spirit, and since one of the authors is a music therapist, we present our findings in dialogue format as a more direct window into this perspective, which is unique among the chapters in this collection. We address the following questions: What are the principles and practices of an improvisational pedagogy for creative music-making with long-term care residents? Is it possible to plan for the unexpected in later-life music-making workshops?