Across countries, the age and timing of when children navigate school transition varies, as does provision of support during this challenging time. These two factors can heavily shape young people's adjustment, yet to date there is minimal research which has investigated how this period is navigated in different cultures. The aim of the present exploratory-explanatory case study was to explore how educational transitions are managed and supported within the US, with a view to apply the lessons learnt to the UK context. Parents in the US have more choice regarding the age and timing of when children transfer schools, and so the research examined differences in transition preparations and experiences by children's age, and whether they are in a two or three-tier school system. To do this, data collection methodologies included ethnographic classroom observations, student focus groups and staff and parent interviews, which were analysed using Thematic Analysis. Findings demonstrated that the earlier the transition, especially between the ages of 11 and 12, the harder it was perceived to be, and stakeholders had differing attitudes as to whether two transitions are better than one. It was concluded that while the present study has made preliminary progress in exploring the significance of transfer timing on students' adjustment, further longitudinal and intervention comparative research is needed using wider cross-cultural samples.