Developed countries are seeing advances in automation and, at the same time, their populations are aging. In this paper we examine both phenomena using the delay in retirement age as a nexus. Although automation is freeing workers from repetitive, hard work, older workers feel threatened by new automation advances which generate skill mismatches. Two links are highlighted: First, since skill mismatches affect low-skilled older workers more than those who are highly skilled, the latter will remain active for a longer period of time while the former will be pushed to retire. Second, the highly skilled workers who decide to prolong their working lives are a valuable resource for further automation advances because this technology continues to need human-assisted solutions. Our analysis establishes an important role for adult training to fill the gap between initial education and the demands of a rapidly changing labor market in order to encourage individuals to postpone their retirement and, hence, to ensure the sustainability of the social insurance system.