The transition from school to work can be crucial in the lives of young people. The ages of 14 – 16 can be a pivotal moment for young people and the choices they make regarding their post-16 transitions. The process of transition requires being able to make a number of important decisions such as whether to continue into further education, leave school, continue to vocational training or university. Growing up, Service children can face a myriad of circumstances that any other child could never imagine, from high mobility to disrupted learning and parental deployment, risking the ability to successfully transition into post-16 destinations. With an estimated number of over 120,000 children from armed forces families in the UK the need to ensure that the needs of these children are addressed in terms of emotional and wellbeing needs and support for attainment and careers guidance is imperative. Between 2020 and 2022 research was undertaken in Scotland and Wales to explore what support is available and needed for Service children to help them transition successfully post-16 and what implications being a Service child has on attainment and aspirations. Drawing on data derived from 19 interviews and 14 focus groups with stakeholders, military personnel, teachers, and Service children, this paper explores issues faced by Service children, and how these can act as barriers to post-16 transitions. It argues that there are many contextual factors affecting the lives of Service children, which should be acknowledged to better support Service children following their departure from school.