Based on participant observation of three projects differing in duration, target audience, theme, objectives and resources, this article seeks to contribute to a reflection about the role of a leader of community music projects in a prison context. We will briefly describe three different musical projects that took place during 2013 in two Portuguese prisons: two projects associated with the Casa da Música (CdM) in Porto – (1) A Casa vai a Casa at the Estabelecimento Prisional do Porto (six sessions between January and March 2013) and (2) Consagração da Primavera at the Estabelecimento Prisional Especial de Santa Cruz do Bispo (twelve sessions between January and May 2013) – and (3) the project of Magna Tuna Cartola at the Estabelecimento Prisional Regional de Aveiro (three sessions in February 2013). From these experiences and based on a comparative analysis of data collected in the different projects, we seek to identify the working strategies used by each of the musical leaders and present a reflection on how they were used in different dimensions of each project. The discussion takes place around two main aspects: (1) the strategies used to guide the musical work itself; and (2) the strategies used to promote the relationship and interaction with and between inmates. With the first aspect we include as important ideas: the search for musical refinement, aural and memory work and the use of signs and gestures. With the second aspect, we identify the following issues: group work, creation of bonds, affection and trust and open leadership.