Parents are the primary managers of children's development during their early years and greatly influence how children are primed for school. Therefore, understanding children's school preparation should involve appreciation for the unique developmental histories and perspectives that parents bring to the relationship with the child, with the teacher, and with the school. The purpose of this qualitative study was to explore mothers' memories of their own schooling and how those memories currently influence their behaviors in preparing their children for school. Forty mothers with preschool-aged children participated in a semistructured interview on their school-related histories. Analyses of the interviews revealed four themes related to mothers' own memories as the most meaningful in guiding their behaviors in preparing their own children for school: (1) intergenerational influences, reflecting how they, themselves, were primed for and supported through school, (2) transitions between school settings or grade levels as sensitive periods, (3) school settings, including characteristics of schools they attended and goodness of fit, and (4) diversity, particularly lack of diversity or an appreciation of diversity in their own schooling. Findings underscore the importance of understanding parents' educational histories in order to better understand children and highlights the types of memories that may be most lasting and influential for mothers as they prepare their children for school. We discuss implications for educators to strengthen family connections, as well as implications for future research. (Contains 1 table.)