The purpose of this study was to investigate the prevalence, sources, and underlying causes of work-related stress among headteachers in Wales and to identify possible solutions. An online questionnaire was sent to all 1588 headteachers across Wales. The questionnaire included demographic questions, Cohen's Perceived Stress Scale (PSS), the Health and Safety Executive (HSE) Management Standards Tool, a list of known stressors, and open questions exploring the underlying causes and possible solutions. A total of 359 (22.6%) headteachers completed the survey. Two-thirds of participants reported experiencing levels of stress that were rated as 'high'. Pressures of managing greater demands and increasing workload with fewer financial resources and a lack of support from local authorities were the main sources of stress. Solutions focused on improved funding to enhance staffing and resources at a school level, reduced accountability, and improved support. The findings indicated that a multi-faceted, multi-level, intervention approach, extending beyond improving personal resilience and individual school improvements, into regional and national opportunities for change, is likely to be most effective in reducing work-related stress within the profession.