The present study aimed to explore the relations between parental and children’s character strengths and children’s school adjustment during the critical period of school entry. Participants were 479 parents and 16 firstgrade teachers of 479 first-grade schoolchildren from five public elementary schools in Israel. Children’s and parents’ character strengths were measured by parental questionnaires based on the Values in Action inventories of strengths. In addition teachers completed questionnaires about their students’ cognitive social emotional and behavioral school adjustment. Findings showed that parents’ intellectual interpersonal and temperance strengths were positively related to their children’s school adjustment. In addition children’s intellectual interpersonal group-interaction temperance and transcendence strengths were positively related to broad aspects of first-grade adjustment. The present study provides an initial exploration of the contribution of personal and parental strengths to young children’s optimal adjustment to elementary school.