This article investigates transition practices from preschool to elementary school for 288 students in Italy who attended Reggio Emilia-inspired preschools. The study evaluated four outcomes: academic achievement, school liking, cooperativeness, and problem behaviors before and after the transition at 2 months and 9 months. The results showed academic achievement decreased after transition but increased in the second year. School liking did not significantly change overall but varied between schools. Cooperativeness increased after transition. Problem behaviors decreased significantly in the first year, especially for schools with high-quality transition practices mandated by Italian law. Overall, better student adjustment correlated with schools having more developed transition procedures between preschool and elementary school.