The chapter presents a comparative analysis of the relationship between youth transition and social security in Japan, Germany, Switzerland, the United Kingdom and Norway. Firstly, it provides an overview of social expenditure on youth-related policies, offering context for understanding social security provisions for young people. Secondly, it examines how social security and labour market policies have evolved in response to emerging social risks affecting young people without access to social insurance. Thirdly, it interrogates the rate at which out-of-work young people receive unemployment-related benefits and social assistance, highlighting differences in benefit coverage among the respective countries. Fourthly, it explores family policy, which is closely tied to parental responsibility for young people, re-considering the dichotomy between familialised and individualised approaches in social policy. Finally, using Japan as a critical case study within youth welfare regimes, the chapter proposes a new typology based on the degree to which youth policies are institutionalised. The framework enables a re-evaluation of the Eurocentric perspective that has been dominant in comparative youth research.