Objectives: This study aimed to examine the cumulative disadvantage of different forms of childhood misfortune and adult-life socioeconomic conditions with regard to trajectories and levels of self-rated health in old age and whether these associations differed between welfare regimes (Scandinavian, Bismarckian, Southern European, and Eastern European. Method: The study included 24,004 respondents aged 50 to 96 from the longitudinal SHARE survey. Childhood misfortune included childhood socioeconomic conditions, adverse childhood experiences, and adverse childhood health experiences. Adult-life socioeconomic conditions consisted of education, main occupational position, and financial strain. We analyzed associations with poor self-rated health using confounder-adjusted mixed-effects logistic regression models for the complete sample and stratified by welfare regime. Results: Disadvantaged respondents in terms of childhood misfortune and adult-life socioeconomic conditions had a higher risk of poor self-rated health at age 50. However, differences narrowed with aging between adverse-childhood-health-experiences categories (driven by Southern and Eastern European welfare regimes), categories of education (driven by Bismarckian welfare regime), and main occupational position (driven by Scandinavian welfare regime). Discussion: Our research did not find evidence of cumulative disadvantage with aging in the studied life-course characteristics and age range. Instead, trajectories showed narrowing differences with differing patterns across welfare regimes.