This article investigates the life satisfaction consequences of migration through unique comparisons of “settler” migrants spanning three family generations and multiple European destinations with their “stayer” and “returnee” counterparts based in the origin country of Turkey. The data are drawn from 5,980 personal interviews conducted as part of the pioneering 2000 Families Survey. The results show that despite being monetarily the most impoverished across all destinations and generations studied, the settlers tend to be more satisfied with their lives than the “stayers” and the “returnees.” However, a downward trend is observed among younger generations, irrespective of their migration status and country context. The results confirm the significance of poverty and asset status for migrants’ and their descendants’ appraisal of life, as well as highlighting the independent effect of the context. Strikingly, however, those residing in countries with more generous welfare states proved not necessarily to be more satisfied.