The scientific debate on social investment (SI) is moving from an ideological and normative approach towards a more realistic one. Scholars are paying closer attention to the actual developments in social policy and to the contextual conditions and impacts of SI policies. Considering this, two main issues arise. First, that SI policies are politically feasible and likely to have positive impacts only if specific contextual conditions are met. Second, SI policies were supposed to have a positive impact on both inequalities and economic growth: a strong theoretical assumption that needs to be carefully tested. The Italian case will be used here to illustrate this new perspective and the consequences of the lack of contextual pre-conditions. For this reason, the article is divided into three parts. The first part will present our theoretical argument in the context of the most recent analytical accounts of SI policy in Europe. In particular we will argue that, given the lack of crucial structural pre-conditions, SI policies may have ambiguous and even unexpected negative impacts on both economic growth and equal opportunities. In the second and third parts, we will present empirical evidence of this ambiguity considering childcare and apprenticeship reforms in Italy. More specifically, based on empirical research carried out in Italy, we want to answer two questions: (1) Why is the Italian welfare state so ‘unfriendly’ to SI policies? What are the main factors explaining the limited room for SI policies? (2) When an SI approach is promoted in specific policy areas in Italy, what is its social and economic impact? Do these interventions achieve the positive results to be expected according to the SI approach? Finally, the last part synthesises the main arguments and aims to open a critical discussion on the structural pre-conditions of SI policies and the need for further analysis of the political economy contexts in which SI policy develops.