Accommodation centres for those seeking asylum present particular contexts in which to facilitate music making. Contextual and systemic difficulties abound. An exploration of a music project within six asylum seeker centres in Ireland is presented with a focus on the experiences of the four facilitators involved. Data are presented from facilitator reflective logs, researcher observations and recorded professional development sessions to uncover the complexities, dilemmas and opportunities that working in such contexts brings. While the facilitators adopted flexible and responsive ways of working, this was not always an easy process for them. Findings reveal some struggles the facilitators had with negotiating new ways of working and 'letting go' that actively involved the singers in the process. This often challenged their previous experiences, beliefs, assumptions and knowledge of learning relationships and pedagogical approaches. The importance of place-based and process-centred approaches to working in such difficult contexts is thus highlighted. The study calls for professional development structures and reflective practice to be embedded within such projects from the outset. Therefore, the findings are particularly important for the design and delivery of projects that seek to engage marginalised communities in meaningful ways.