Internationally, there is growing interest in children's transition to school and their readiness for formal education. Parents' memories of school offer important insights into children's preparation for school and how families view schools; however, few studies consider the influence of educational histories. To address this gap, a sample of 24 parents (16 mothers, 8 fathers) from lower income backgrounds were recruited to discuss the process of preparing their child for kindergarten and their recollections of school. During semi-structured interviews, parents shared their recollections of school and identified links between their memories and their current thoughts and behaviours as they prepared their child for school. Based on a thematic analysis of interview transcripts, three types of memories emerged as the most robust and meaningful in preparing for children's school entrance: (1) the influence of school transitions, (2) the social side of schooling and (3) special education labels. Experiences parents recall from their many years of first-hand exposure to school settings appear to impact the way they prepare children for school and their relationship with the school community. Suggestions are offered for school personnel and future research in this area.