Abstract: Education is recognized as a critical factor in children’s future life opportunities. However, there is a significant gap between the educational performance of Indigenous and non-Indigenous Australian children that perpetuates the recognized disadvantage. One strand of the National “Closing the Gap” initiative is that of supporting Indigenous early childhood development, with this approach recognizing the critical importance of the earliest experiences of children with school to their longer term achievement. Parents and Learning (PaL) is one home-based program, developed by the remote Indigenous Napranum PaL Group, which engages Indigenous parents and caregivers in their young children’s early literacy learning. In this program Indigenous tutors link with parents in their homes to provide regular reading activities for the children, with tutors supporting the parents in the use of these materials. This program operates at the level of school readiness through a strengthening in the child’s literacy skills and school behaviours, with parents developing a greater capacity to support their children’s learning and a stronger engagement with the school environment that will support their child across the transition. This paper explores the experiences of parents and students across this transition experience. Findings to date have shown higher levels of literacy achievement of the children involved in PaL and also more positive involvement by parents with preschool school and also in their community – assisting in overall school readiness. Data from interviews of parents and children provides reflections on how the children and parents differentially experience the transition into school, adding to the understanding of the key elements of the preparation process, and the identification of possible strategies that could be implemented to further support parents and children across this process for more successful outcomes.