Abstract: Infrastructure to support the educational experiences of children and youth living in Canadian military families has ebbed and flowed over time. With the launch of initiatives, such as Seamless Canada, in recent years and the recent restructuring of support infrastructure in the Department of National Defence, it appears that the educational experiences of military-connected children and youth are once again becoming a priority. However, without knowledge and awareness of past efforts to support the educational experiences of these children and youth, present-day challenges faced by the Canadian Armed Forces may make forward progress more difficult. Using the Second World War Canadian military, particularly the Royal Canadian Air Force (RCAF), as a historical example, this article provides lessons learned and future considerations for supporting the educational experiences of children and youth from Canadian military families.