This study analyses the position of people over 44 years of age in the Basque labour market in terms of the type of occupations performed and their skills. The results identify a particularly disadvantaged sub-group of people over 44 years of age: the chronically unemployed. This group was previously employed mainly in occupations that have lost weight in total employment in recent years, also known as declining occupations. Some of these occupations have been subject to automation processes, which are increasingly present in a labour market subject to growing digitalisation. The study identifies certain occupations from which a large proportion of chronically unemployed people originate, especially the over-44s. More manual occupations, such as “cleaners and assistants”, are the source of a higher proportion of chronically unemployed people. Cognitive skills, which are more difficult to replace by automation processes, are also less present among the chronically unemployed. The results highlight the need to address the skills that the target group lacks in order to move towards jobs with positive future prospects at the lowest possible cost.