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World Values Survey data is used to test the association between urbanization, operationalized as population size, and subjective well-being, operationalized as life satisfaction, in the case of Egypt. Regression results show that the smallest settlements have the highest positive effect on subjective well-being compared to the large urban centers. These results are persistent even after controlling for an extensive set of socio-demographic variables. Another important finding is that the two main urban and economic centers of the country, the Greater Cairo and Alexandria regions, generate lower subjective well-being when compared to the more rural regions (Lower and Upper Egypt). These results are both unexpected and compelling, especially in the context of a developing country such as Egypt—previous research argues that cities should generate higher subjective well-being when compared to rural and township settlements in such a context. Our empirical findings show otherwise and provide a novel and crucial contribution to the literature on the subjective wellbeing- urbanization nexus. [ABSTRACT FROM AUTHOR]