This chapter explores the management of cultural diversity within the legal system, focusing on the complexities faced in family law in Italy. Multicultural societies, characterized by diverse cultural, linguistic, and religious backgrounds, challenge traditional legal frameworks: against this backdrop, it is highlighted the critical role of intercultural mediators, who help bridge gaps between immigrant communities and legal institutions, ensuring better understanding and communication. Based on semi-structured interviews with lawyers and judges in Milan, the chapter provides empirical insights into the practical difficulties encountered when addressing cultural diversity in legal cases and the limits when involving (or trying to) intercultural mediators. Several challenges are identified, such as the lack of formal status, standardized training, and institutional recognition for these mediators, which hinder their effective integration into legal processes, discussing how these challenges impact the fairness and efficacy of legal proceedings.