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This study examines how gendered life course trajectories in education/employment and family formation shape later-life health, and whether the health returns to these trajectories vary with macro-level gender inequality. Using retrospective life histories from the Survey of Health, Ageing and Retirement in Europe (SHARE), we apply multichannel sequence analysis to identify typical life course patterns and link these trajectories to later-life health outcomes. We integrate year-specific country indicators of gender inequality into a regression framework with country and period fixed effects, identifying effects from within-country institutional change. Results show that employment-discontinuous and early family trajectories are associated with poorer health, particularly for women, and that declines in gender inequality attenuate these penalties. The findings demonstrate that gender inequality modifies the long-term health consequences of life course trajectories and highlight the importance of institutional context for gendered health inequalities.