In their move to school, children and their family are faced with significant changes in their relationships, environment and routine. In this article, the experiences of a group of children transitioning into a new entrant (NE) school classroom from their early childhood centre (ECE) are discussed. As they began adapting to the new social and geographical climate of school, the use of digital images and transitional objects became a foundational tool to support them in forming a connection and sense of belonging in this new place. Through the combination of these images and transitional objects there is potential to support their roleplay, enabling them to rehearse social and geographical scenarios that are affecting them in their world. This article will discuss that play is the medium through which children can show teachers where they are in their understandings, in effect planning their own next steps in their transition journey. This emphasises the importance of the NE teacher observing children's play to provide a thorough and responsive transition plan.