A successful start to school correlates with positive later educational outcomes, both social and academic. Transitioning experience differs according to social context and this study was conducted in the UAE. Expatriate teachers, UAE national parents and expatriate parents were asked to complete a questionnaire of 20 child behaviours indicating the degree of agreement that each would indicate a successful transition. Differences according to role (teacher/parent) or culture (UAE national/expatriate) were found. The experience of transitioning is a highly context dependent phenomenon and each context warrants investigation to ensure as positive a start to school as possible for each child.