This study investigates how Hofstede’s five cultural dimensions, Power Distance, Individualism vs. Collectivism, Masculinity vs. Femininity, Uncertainty Avoidance, and Long-Term Orientation, influence user satisfaction in online shopping within Madagascar and Indonesia. Using a quantitative approach, data were collected from 106 respondents (54 from Madagascar and 52 from Indonesia) and analyzed through multiple regression and independent t-tests to identify both country-specific and cross-cultural patterns. The results reveal that Power Distance, Uncertainty Avoidance, and Long-Term Orientation are significant predictors of online shopping satisfaction in both countries. These findings suggest that consumers in hierarchical and risk-averse cultures tend to value clear authority structures, secure transactions, and consistent service quality. In Madagascar, collectivist tendencies significantly contribute to satisfaction, as users rely heavily on social recommendations and informal trust networks. In contrast, Indonesian consumers’ satisfaction is more strongly associated with institutional trust, platform reliability, and long-term engagement, reflecting the country’s more mature e-commerce ecosystem. Masculinity vs. Femininity was found to have no significant effect in either context. The study concludes that while some cultural dimensions universally affect user satisfaction, others operate differently depending on each country’s social and technological environment. These insights emphasize the need for culturally adaptive e-commerce strategies that integrate risk reduction, authority signals, and long-term customer relationship programs. Future research should expand the sample size, particularly for Indonesia, whose larger population warrants broader representation, and include additional variables such as trust in technology, digital literacy, and platform usability.