Rationale: It is often assumed that experiencing an upward shift in social position from one generation to the next will bring happiness, yet empirical evidence for this is limited. Objective: We provide a large-scale test of the relationship between intergenerational mobility and midlife life satisfaction using data from two prospective UK studies (N = 20,948). Method: Intergenerational mobility was modelled as a formative construct gauging the extent to which individuals moved up or down the social hierarchy compared to their parents, on a continuum ranging from high levels of downward mobility to high levels of upward mobility. Results: An intergenerational increase in social mobility, captured by greater educational attainment, social status, and home size than one’s parents was positively associated with life satisfaction at age 42 in both cohorts. Mediation analyses revealed that almost half of this relationship was explained by better self-reported health and fewer perceived financial difficulties amongst the upwardly mobile. Conclusion: This study provides evidence that enhanced satisfaction with life may be a key outcome of intergenerational increases in social status.