The transition to kindergarten is foundational for children's future school performance and families' relationships with the educational system. Despite its well-documented benefits, few studies have explored family engagement across the pre-Kindergarten (pre-K) to kindergarten transition nor considered the role of geographic context during this period. This study examined trajectories of family engagement across the pre-K to kindergarten transition, and identified whether engagement differs for families in rural versus urban settings. Participants were 248 parents of children who participated in publicly funded pre-K programs and transitioned 1 year later into kindergarten. Home-based involvement increased from pre-K through kindergarten. School-based involvement increased during pre-K and decreased through the end of kindergarten. Structural and relational communication remained stable during pre-K and decreased through the end of kindergarten. Compared to urban parents, rural parents reported less home-based involvement, structural communication, and relational communication. Implications for practice and policy are explored. [For the corresponding grantee submission, see ED602471.]