This is a participatory action research study within a critical realist paradigm, developed to work with a group of Newcomer workers in a settlement sector agency in Canada, to understand the complex set of forces that affect their wellbeing at work, and to make reccommendations for improvement to the organization. The study was comprised of two PAR cycles – one with an initial group of six Newcomer workers at a single organization, and a subsequent cycle with four more Newcomer workers at different organizations. The study found that within this group of workers, the workers unanimously stated that the barriers in the settlement sector system, the barriers to accessing resources in the local community that they and their clients face, and the disconnect between the workers and the organization, had a far greater impact on their wellbeing than their clients’ stories of trauma and loss. The workers expressed the importance of their connections with their clients, which increase the meaningfulness of their work. This meaningfulness, along with their fears of setting boundaries as Newcomers, create a system where the workers donate large amounts of unpaid work as well as provide care to their communities in the off-work hours. With the high level of stressful work, combined with constant changes in the system, there is a disconnect between the workers’ focus on their clients’ needs, and the management’s focus on the needs of the funder, resulting in the workers’ needs not being well met. The group developed recommendations to address particular stresses at the organization level, and outcomes were shared with organization management, the team of supervisors, and the larger staff of Newcomer workers.