The current economic crises incredibly enhanced the destandardisation of life course and made the transitions among the passages riskier. It has made those who share perilous social locations in social space more vulnerable. This chapter concentrates on the intersectionality of youth, migrant and gender statuses across various welfare regimes in the European Union and analyses how these regimes respond to the growing destandardisation process for this group, particularly in school-to-work transitions. It reveals that young migrant women are negatively affected in each of the welfare regimes analysed. Universal regimes, mainly characterised by an institutionalised vocational education training and strong counselling support, perform relatively well in facilitating school-to-work transitions of different vulnerable groups. The chapter concludes that the inequality in school-to-work transitions is strongly associated with broader structural issues and, therefore, comprehensive approaches, rather the policies targeting singular areas, are needed.