We examine how both the welfare regime and health affect retirement trajectories in countries with flexible retirement policies using longitudinal methods and harmonized panel data from two social-democratic (Sweden and Denmark) and two liberal welfare regimes (Chile and the United States). An early retirement trajectory, which represents retirement in the early 60s, is the most frequent in all countries, although it is less prevalent in liberal than in social-democratic regimes. Adverse health conditions are more frequent among early retirees in liberal but not in social-democratic regimes. Overall, we do not find evidence for an inciting effect of flexible retirement policies on working life extension. However, welfare regimes substantially affect late-life labor force participation.