The article focuses on social vulnerability and how Lifelong Learning (LLL) policies tackle it. Two Italian case studies on local LLL measures within Italian Youth Guarantee (YG) scheme are discussed: Civic Service in Genoa and NEETwork Project in Milan. The aim is to investigate how such measures shape the life courses of young adults in vulnerable conditions. Examining whether their support of the school-work transitions meets the youths' needs, accounting for the different contexts and the individual resources and shortcomings. Similarities and differences between the two case studies are discussed, focusing on policies' governance and concept of vulnerability applied to young adults. A conceptualisation of the vulnerability as a process developing over the young adults' life course trajectories is presented. Conceiving it in a multidimensional way, discussing the interplay between the individual resources, and contextual factors in emerging 'vulnerable conditions' of young adults. Then, the article proposes possible interpretations of the ways in which young adults relate to and cope with LLL policies, according to the Merton's strain theory, outlining different strategies of adaptation in uncertain biographies. The risk to increase social exclusion and inequalities is discussed as an unintended effect of LLL policies.