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The identification of barriers for e-commerce to thrive in specific countries is a topic of great interest. This work proposes two models to study the barriers to B2C e-commerce adoption in Portugal, highlighting obstacles less exploited by previous research: the impact of offline shopping pleasure and the influence of the distance to shopping malls on online shopping intent. An online survey was conducted based on different constructs. A multivariate OLS hierarchical regression was used to analyse the proposed models regarding the intention to buy online and the number of online purchases. The results revealed that customer satisfaction is a strong predictor of intent to buy online and that perceived product risk remains a barrier to e-commerce. Consumers living in high urbanised areas have more propensity to buy online. Helpful information is provided regarding the impact of context, culture, product, and individual barriers, showing that multichannel strategies are best suited for success.