Community Orientated and Opportunity Learning (COOL) Music was a 12-month collaborative project between researchers at Glasgow Caledonian University and practitioners at the Edinburgh-based social enterprise Heavy Sound. The project began in October 2017 and involved 16 sessions of participatory music making with 32 ‘hard-to-reach’ young people (aged 12–17) aimed at increasing confidence and self-esteem and improving social skills. Using COOL Music as a case study, this article explores some of the challenges faced by community-based arts organisations tasked with delivering such interventions, contrasting COOL Music’s small-scale, targeted, community-based approach with prevailing top-down music interventions in Scotland. We argue that such programmes are particularly suitable in engaging those at the margins of society, reaching them on their own terms through music that resonates with their own lived experience. However, we acknowledge the short-term and transitory nature of such projects may prove problematic for some hard-to-reach groups who require more stability in their lives and may also lead to staff fatigue and burnout. We call for further research in these areas, and greater policy attention to be paid to the sustainability of such projects.