The digital gender divide is facing new challenges in the fluid context of a transformative labour market, population ageing, and the extended working life. The topic deserves a comprehensive and actual analysis using a ‘digital lens’. This chapter illustrates how digitalisation is connected to the existing challenges of gender and age in the working life and in the context of other structural factors. By performing a critical analysis of global and European data, research, policies and practices on gender, digitalisation, and the working life, the authors identify possible opportunities, risks, and ways forward. National data from the United Kingdom, Hungary, and Romania are analysed relating to the structural foundation of the digital gender divide and to support better policies that mirror the inter-influences of gender, ageing, and digitalisation and result in a digital gender working balance.