Background: Economic disruption in East Germany at the time of reunification (1990) resulted in a noticeable increase in unemployment. The present study provides data from a German cohort for over 20 years. The aim was to examine how the frequency of experiencing unemployment affects life satisfaction and whether their relationship changes over time.Methods: In the Saxon Longitudinal Study, an age-homogeneous sample was surveyed annually from 1987 to 2016. Since 1996, 355 people (54% female) have been examined for issues related to unemployment. Life satisfaction was measured with both the Global Satisfaction with Life Scale and the Questions on Life SatisfactionModules questionnaire.Results: In 1996, the participants were 23 years old and 50% of the sample was affected by unemployment. At all 16 different measuring points, participants who were never unemployed indicated higher life satisfaction than those who were once unemployed. The repeatedly unemployed consistently reported the lowest values of life satisfaction. In each year, there were significant differences with small to medium effect sizes.Conclusion: Our results support the notion that the adverse effects of unemployment on life satisfaction increase with the time spent unemployed. In 2016, only 2% of the cohort were currently unemployed, but differences between people with and without unemployment experience still exist. This indicates that the negative effect of the unemployment experience will last for a very long time. To the best of our knowledge, this is the first study that demonstrates the effect so persistently at so many measurement points for over 20 years.