Rights of the elderly have been judged from a changing perspective in recent decades. On the one hand, the aim is to ensure an active role for them through the intensive use of welfare instruments. On the other hand, it is important to improve the situation of ageing societies by keeping ageing generations in the labour market and easing the burden on pension systems. It is a contradiction that no developed country has yet resolved this. The labour shortages and digitalisation can be observed as new challenges. Older workers are more exposed to the risks arising from these phenomena than the younger workforce. The European Pillar of Social Rights builds protective mechanisms to strengthen the workers’ legal status, and the Framework Agreement on Digitalisation tries to prepare everyone for the effects of AI and digitalisation, however, these solutions cannot be equally effective for different generations. The European Union law regulation of active employment does not contain additional elements for the protection of the elderly that would stabilise the labour market opportunities of the older generations. In principle, there is a need to employ pensioners, while it is a well-known fact that the chances of employment decrease significantly with advancing age. In the labour law regulations, we cannot find such targeted reliefs either in terms of working time or remuneration. The aim of the paper is to highlight these legislative and economic inconsistencies and to make recommendations for decision-makers in the field of employment. The research method contains the analysis of the recent social policy legislation of the EU, fragments of the relevant case law of the Court of Justice of the European Union and some current provisions of Hungarian labour law. The main research question of our paper is as follows: how the crucial social rights of older workers can be effectively enforced in these changing labour market conditions. The analysis is based on the market, legislative and enforcement perspective at the same time. Moreover, the challenges generated by the digitalisation of work are also present in our paper.