In Australia, eligible long day care services may apply for support at the state level to assist with the transition of children from culturally or linguistically diverse backgrounds into childcare settings. For staff in childcare services, this support comes in the form of a cultural support worker (CSW). The primary role of a CSW is to build capacity in childcare staff to support children and families as they enter the childcare program. This paper draws on interview data and documentation from multiple sources to report the perspectives of key stakeholders affiliated with a cultural support program in an Australian childcare setting. It concludes that a more flexible approach to policy that directs the work of CSWs is needed, as well as further research into ways to build capacity for cultural competence for both CSWs and childcare staff who work collaboratively to support young children as they transition to childcare.