The project On the Wings of a Piano . . . I Learn to Fly was developed with four women in custody inside a Portuguese prison during 2013–2014 over a period of eight months. Weekly individual sessions focused on improvisation, composition, memorization, and learning repertoire. This one-to-one work with participants resulted in the presentation of three distinct public performances in different contexts and for different audiences. Community music principles of decentralization, accessibility and equal opportunity were the foundation of a strong triangular relationship between the participants, the music they played on the piano, and the facilitator. With the narrative of each participant at its core, this article explores different ways in which this project can be identified as community music, despite the emphasis on individual work with each of the participants. The importance of adapting to each participant’s personal needs, requests and skills is highlighted, as well as the value of the affection developed between facilitator and participants. The subjectivity inherent in the involvement of the facilitator as a researcher is discussed, and the pedagogic outcomes of the project are also considered as an important contribution to research on music in prisons.