How are safety and risk negotiated within community singing? Many group facilitation techniques within adult education take as foundational that participants must feel safe to participate fully in group learning. This concern for participants’ safety acknowledges that power and privilege circulate unequally within any social learning context, shaped by race, gender, class, ability, sexual orientation, and in the case of singing, musical competencies. However, community singing can be safe without being comfortable. Comfort, therefore, is not the same as safety, although the two concepts are often conflated. A lack of ease with the process and/or content suggests a possibility of risk for learners as they brush up against the edge of what they know. In this paper, I argue that along a continuum of, on the one end feeling both safe and comfortable, and on the other end feeling unsafe (which inherently suggests extreme discomfort), the deepest musical and social learning constantly negotiates a tension between safety and discomfort. Using Joyce’s analysis (2003) of safety in community singing contexts as my point of departure, I will unpack the concept of safety within musical learning contexts, and how safety is related to, but distinct from, comfort and risk. I will then look specifically at community singing for adults and the particular challenges and possibilities negotiating safety and risk that this context offers. Finally I interrogate whether a balance of safety and risk can truly be achieved for a group of learners who occupy diverse and often oppositional subjectivities. Community singing facilitators grappling with social and cultural considerations of safety and risk create sites of troubled learning for participants, moving beyond the technicism of vocal skills-building towards fostering transformative learning through song.