As founder of modern political economics and prominent theorist of the commercial society, Adam Smith’s importance is universally recognized. Little, however, has been done so far to develop Adam Smith’s virtue ethics in the context of modern business, characterized by digitalization. This article aims to rediscover Adam Smith’s virtue of prudence and its relevance for the “e-commercial society”: It presents a framework that considers the central place of prudence in the relationship between a prosperous e-commercial system and societal flourishing. In Smith’s view of the commercial society, prudence enables people to develop habits of character related to industriousness, genuineness, spirit of sacrifice, and self-command, which help in the conduct of a prosperous business activity. This article translates Smith’s virtue of prudence into a language typical of consumers in the current e-commerce scenario, considering their development as persons and the contribution of their activities to the good of society.