Institutional exit pathways shape individual trajectories from work to retirement. In the Netherlands, early retirement schemes as well as disability and unemployment benefits structure the timing and complexity of transitions within such trajectories. Simultaneously, access to these exit pathways depends on the individuals’ entitlements to various social security programmes as well as their freedom to decide on the timing and path of exit. In this study, sequence analysis was applied to register data of primary sources of income with the aim of identifying the main trajectories from work to retirement between the ages of 56 and 66 for a sample of Dutch men and women born between 1943 and 1945 (N = 2,277). Seven distinct trajectories were found: ‘early retirement’, ‘premature retirement’, ‘late retirement’, ‘disability’, ‘unemployment’, ‘inactivity’ and ‘drop-out’. Multinomial logistic regression analysis was applied to investigate the relations of these trajectories with a set of individual and socio-economic characteristics, as well as factors at a firm level. Especially women, non-natives, the lower educated and the self-employed were found to have a greater risk of ending up in the ‘involuntary’ trajectories of late retirement, disability, unemployment and inactivity. Public-sector employees, farmers and craftsmen, and skilled blue-collar workers were less likely to differentiate from the norm of entering into premature retirement between the ages of 60 and 64.