Art and music-based activities have played an important role in social work with groups since the origin of the profession. These activities continue to be used, yet less in known about how they are facilitated and led. This International Association for Social Work with Groups SPARC endorsed and funded study responds to this gap in the literature by examining the development and implementation of group-based music education residencies. Classically trained teaching artists (TAs) from a Chicago-based music ensemble led and facilitated a series of residencies at one agency with a drop-in center and a transitional living program for emerging adults experiencing homelessness and other forms of housing instability. Qualitative methods, including observation and focus group interviews, were used to explore the development and implementation of the residencies. Findings suggest TAs’ adaptability, which is defined as flexibility, role adaptability, and capacity to meet residency participants where they were, played an important and integral role in the residencies. This study adds to the existing literature on music-based activities in social work with groups and extends our understanding of how these activities are facilitated and led.