While a prolonged working life has been mainly feasible for people with the most advantageous working careers, knowledge about the barriers for those with vulnerable occupational paths is still scarce. This study explores the conditions for prolonged working life from a perspective on labor market trajectories. Drawing from a gendered life course perspective and that (dis)advantageous tends to accumulate over time, we investigate the opportunity structure for the most disadvantaged workers and which characteristics of labor market trajectories can explain the decision to work longer. To this end, a Swedish longitudinal survey and register data from the Panel Survey of Ageing and the Elderly (PSAE) were used, following people across a substantial part of their working life. With sequence analysis, we identified 5 trajectories that represent typical labor market trajectories from mid-life until retirement age. Our findings showed that labor market precarity in mid-life remained a key characteristic until the expected retirement age, showing both early signs of early labor market exit and a precarity trap into a prolonged working life. These findings emphasize the need to identify at-risk groups early in their careers and that mid-life interventions are needed to prevent involuntary labor market exits and to ensure a sustainable working life. In particular, the need to protect older workers with turbulent or precarious labor market trajectories against labor market risks and retirement schemes that could inadvertently contribute to increased social and economic inequality in later life.