Early intervention to support mental health and well-being of school-aged children may be of significant benefit in preventing escalation of mental health problems in later life. While there are limitations to current understanding of the best ways for schools to support mental well-being, a whole school approach (WSA), involving all those who are part of the school system in creating and sustaining a supportive environment where health is prioritized, may be effective. This research explored stakeholder views of this approach, as part of a contract commissioned by the Welsh Government to conduct an evaluability assessment of a WSA. Semistructured focus groups and interviews were completed with stakeholders from the health and education sectors, as well as parents, to explore how a WSA may operate in a Welsh context and barriers and facilitators to potential implementation and outcomes. Findings suggest that existing pressures on schools may impact implementation of a WSA, with school staff already time poor and many staff experiencing their own mental well-being challenges. Implementation may be supported by clear guidance at local and national levels, funding for staff time and training and stakeholder involvement at all stages. Long-term monitoring and evaluation are also needed to understand system changes.