Lifespan research has long been interested in how contexts shape individual development. Using the separation and later reunification of Germany as a kind of natural experiment we examine whether and how living and dying in the former East or West German context has differentially shaped late-life development of well-being. We apply multi-level growth models to annual reports of life satisfaction collected over 20+ years since German reunification from 4,159 deceased participants in the Socio-Economic Panel (N[subscript West]= 3,079, M[subscript age at death] = 73.90, 47% women; N[subscript East]= 1,080, M[subscript age at death] = 72.23, 48% women). We examine differences between East and West Germany in levels, rates of change, and onset of terminal decline in well-being and the role of age at death, gender, education, disability and time spent in reunification. Analyses revealed that West Germans reported higher life satisfaction than East Germans, and that these differences get smaller both with passing time since reunification and in late life. The gap between East and West Germany diminishes over the last 10 years of life by more than 25%. Taking into account key individual characteristics only slightly attenuated this pattern, with education and age at death moderating late-life well-being level and decline in East Germany. Our results are consistent with long-standing notions that contextual factors shape individual development and illustrate the plasticity of human development. After having experienced disadvantages in life circumstances for up to 40 years through living in East Germany, effects of this natural experiment diminish considerably with passing time since reunification.