Frontline workers in homeless services work in a high‐intensity, emotionally consuming environment, with frequent exposure to traumatic material with potentially significant consequences for their own mental health. This, in turn, may have a negative impact on the quality of care provided to homeless service users. Prevention of this trajectory may be achieved through psychologically informed environments for staff. This study aimed to explore factors that may influence the development of burnout, secondary traumatic stress (STS), depression, anxiety and stress in this population. Elevated levels of burnout and STS were predicted, as was an association between the predictor variables of professional experience, educational background, continuing professional development, access to organisational support structures and the outcome measures of compassion satisfaction, burnout, STS, depression, anxiety and stress. An online cross‐sectional survey design using the Professional Quality of Life Scale (Version V) and the Depression Anxiety and Stress Scale‐21 and scales designed for this study capturing occupational variables were distributed via email and national networks to a wide range of services across Scotland and the rest of the UK. Over 4 months in 2017, 112 frontline homelessness workers in health, social care and third sector organisations completed the survey. Results did not indicate elevated levels of burnout or STS, though depression and stress were found to be significantly elevated compared to population norms and were associated with burnout, compassion satisfaction and secondary traumatic stress. High levels of various types of supervision support and CPD were identified. There was no association between these and burnout or stress. We highlight the elevated levels of stress and depression and make a research recommendation to parse types of supervision to assess for optimal effectiveness and efficiency in ensuring that staff working in high‐stress homelessness settings receive optimal support to deliver high quality services.