Using sen's capability approach as an analytical framework, this paper attempts to assess and evaluate the dutch measures for facilitating transitions from unemployment to (gainful) employment. This method is particularly useful in the context of the eu's economically informed flexicurity approach to evaluate the institutional preconditions for effective participation in the labour market. It will be argued that the existing legal measures alone are insufficient to address the difficulties of reintegrating older (long-term) unemployed persons in the labour market. Measures taken to reactivate older unemployed workers merely build upon economic considerations, such as guaranteeing the sustainability of the pensions and social security schemes. Other (non-economic) considerations are often overlooked. This ignores the actual risks: not actually having access to the labour market entails a variety of risks, not only in terms of job, and thus (a partial) income, loss for the employee concerned, but also for the member states who are obliged to do everything necessary to achieve the eu's goals.