Starting school requires children to manage a wide range of personal, interpersonal and institutional expectations and challenges, yet few child-report measures have captured the diversity of these experiences. In this paper, the Pictorial Measure of School Stress and Wellbeing (PMSSW) interview was used with 101 school entrants at the beginning and end of the kindergarten year to explore children's feelings about typical school events, reasons for these feelings, strategies for coping with these challenges, and the extent to which these perceptions changed over time. Results showed that the majority of children were positive about these aspects of school and did not change their feelings, but a minority were persistently negative, and up to 29% became more negative over time. Responses varied by the type of event, with some being perceived as more challenging than others. The strategies children suggested for managing challenging events offered insights into their understanding and use of school rules and routines as a coping mechanism, particularly at the beginning of the school year. Over time, children showed greater use of personal strengths and abilities, their friendships with peers and their relationships with teachers to suggest effective strategies. These findings confirm the potential of the PMSSW as a tool for gathering children's perceptions of wellbeing and coping at school. Through the use of methods that acknowledge and empower children, researchers and teachers can better appreciate and cater for individual differences in children's experiences of school transition.