This study examines the relations between parent–educator communication and preschoolers’ numeracy, literacy, executive function (EF), and vocabulary, and explores if these relations work through the home numeracy environment (HNE) and the home literacy environment (HLE). Children (48.92% female, M = 57.75 months, SD = 3.71) were either enrolled in a state-funded prekindergarten program (n = 376) or in another community-based preschool program (n = 182). Research Findings: Analyses revealed a significant relation only between parent–educator communication and numeracy skills (β = -.14, p = < .001). Specifically, and unexpectedly, higher parent–educator communication scores in preschool were related to lower numeracy skills. Even though there were no significant direct effects between parent–educator communication and children’s outcomes, we wanted to examine if there were any significant indirect effects. The indirect effects for the HNE and HLE were not significant for all outcomes.Practice: The findings suggest that there may be increased communication when the children are performing lower on their numeracy skills than their peers and teachers and parents are working to remediate those challenges. Consequently, it may be beneficial for educators to engage with families early in the year to support the development of children’s numeracy skills.