Children are more likely to succeed academically, socially, and behaviorally when families are engaged in partnerships with schools and teachers throughout the educational process. Researchers and policy leaders have identified the kindergarten transition as a key time for fostering family educational engagement. This study reports findings from the Kids in Transition to School (KITS) Program designed to promote school readiness and support family engagement with schools. The KITS Program helps caregivers build confidence and advocacy skills that can support successful partnerships with their children's teachers and schools. Prior KITS research has primarily focused on child outcomes, while caregiving outcomes such as family engagement have received less attention. This study adds to family engagement literature by examining the effectiveness of the KITS Program in improving engagement during the transition to kindergarten, as well as examining differences in intervention effects for diverse families, who may encounter cultural, linguistic, and other barriers to engaging with teachers and schools. Results indicated that the KITS Program improved caregiver-teacher relationship quality, caregiver's feelings of positivity towards the school, and support for children's learning at home. In addition, results indicated that the KITS Program was equally effective for Latinx and non-Latinx families. However, Latinx families rated their relationships with teachers and their endorsement of their schools lower than non-Latinx families. Findings from this work support the KITS Program as a promising intervention to improve family engagement during the transition to kindergarten. Implications for practice, policy, and research are discussed.