The importance of children experiencing a successful transition to school is well established in research literature. Central to this is including the children themselves in the conversation about their learning and ensuring they develop a sense of fit and belonging to their new school environment. The findings shared in this paper sit within a larger study of examining children's perspectives of their literacy experiences at the time of transition to school. This paper reports the perspectives of two children, firstly in their pre-school (prior-to-school) setting and then again in their Kindergarten setting (the first year of formal primary schooling in New South Wales). The study draws on the theories of literacy as a social practice and describes literacy as events and practices. Digital storytelling was used as the main data collection method to capture the children's voices as they annotate images, describing their chosen literacy events in each educational setting. Findings revealed that whilst some children have a confident and successful initiation into the literacy events and practices of school, others may not. Herein are substantial messages, firstly, that we need to listen to children so we can support their transition to formal school and secondly that teachers need to better understand the literacy practices of children in pre-school to more effectively support them as they transition to Kindergarten.