Do younger generations face more challenges in the labour market compared to other (older) generations? While European labour markets pursue their trajectory of liberalisation, some argue that all things being equal, younger generations are disproportionately denied the socio-economic rights of job security and stability. This chapter investigates claims of intergenerational disparity in labour market disadvantage in two different post-industrial democracies, Germany and the UK. It introduces a new measure of labour market insecurity that considers contractual commitments and household financial stability. Using a hierarchical age, period, and cohort (HAPC) effects model, the chapter examines inter-generational differences in labour market disadvantage. By comparing Germany and the UK, it reveals important cross-country differences. It finds that in Germany labour market precariousness is divided among generations, with people belonging to the “silent generation” (1935–1945) and “Millenials” (1980–1990) working under the worst labour market conditions. The model is designed to differentiate between generational (birth-cohort) effects and other sources of inequality in the labour market, such as ageing, short-term economic shocks, and changes in the gender and migration composition of the workforce. The chapter calls for the need to address labour market inter-generational inequality to foster cross-generational solidarity and enhance social citizenship rights.