The goal of this study was to track the progress of Italian children at risk for school failure enrolled in preschools based on the Reggio-Emilia approach. Risk factors considered included family socioeconomic status (SES), child receptive language, and child gender. Participants were 211 children (Mage = 60.8 months, 116 girls) in Reggio-inspired preschools in Genoa, Italy. The sample was followed over six time points starting from the last year of preschool (ages 5-6 years) through the end of the second year of elementary school. We examined trajectories of school liking, teacher-child relationships, and teacher-rated language/mathematics. Trajectories of at-risk children were predominantly indistinguishable from those of the full sample. Children at risk because of lower SES and poorer receptive language (but not gender) were rated by teachers as more dependent than children not identified as at risk. Contrary to expectations, children of mothers from low-SES backgrounds liked school more than the rest of the sample.