Purpose: The article describes an evaluation study to test the effectiveness of "Storie in gioco" project (Stories in Play, Storie in gioco [SIG]), a dropout prevention intervention aimed to prevent early school leaving (ESL) in at risk students. Method: The research used a mixed-method approach: in the quantitative phase, a two-group pre-/post evaluation design involving 230 students was used to estimate SIG outcomes; in the qualitative step, stakeholders' focus group discussions and interviews have been used to interpret results. Results: Even if SIG appears to impact scholastic self-esteem and peer relationships, no effect was found when a comparison group matched for baseline measures was used. Based on qualitative data, the article identifies mechanisms influencing SIG outcomes and provides key insights into improving it. Conclusions: The authors emphasize the priority to develop programs to reduce intergenerational transmission of educational poverty and express methodological and theoretical considerations regarding SIG effectiveness and ESL prevention interventions.