The transition from preschool to primary school is a pivotal developmental period in children's and their families' lives. However, not all families have equal access to resources and some parents face additional barriers to the types of transition and school readiness activities they participate in compared families with higher social capital. Using quantitative data from the Children's School Lives (CSL) national longitudinal study of Irish primary schooling, we examined the relationship between social and cultural capital and parents' beliefs and participation in academic school readiness activities with their child. A multigroup structural equation model was estimated with online survey data collected from 477 parents to explore these relationships for first time parents and parents who previously experienced the transition with an older child. Results indicated that school connections through an older child may have an impact on parents' academic readiness beliefs and practices during the transition to primary school, particularly for non-native English speakers, and parents with lower levels of education or occupations. The study highlights the need for clear, culturally sensitive policies and information sharing between schools and first time families about school culture and expectations in order to support families during this crucial developmental period.