Ethical issues surrounding the marketing and trade of controversial products such as tobacco require a better understanding. Virginia Slims, an exclusively women’s cigarette brand first launched in 1968 in the USA, was introduced during the mid 1980s to major Asian markets, such as Japan and Korea, dominated by male smokers. By reviewing internal corporate documents, made public from litigation, we examine the marketing strategies used by Philip Morris as they entered new markets such as Japan and Korea and consider the extent that the company attempted to appeal to women in markets where comparatively few women were smokers. The case study of Virginia Slims reveals that the classification of “vulnerable” consumers is variable depending on culture, tobacco firms display responsive efforts and strategies when operating within a “mature” market, and cultural values played a role in informing Philip Morris’ strategic decision to embrace an adaptive marketing approach, particularly when entering the Korean market. Finally, moral questions are raised with tobacco being identified as a priority product for export and international trade agreements being used by corporations, governments, or trade partners in efforts to undermine domestic public health policies.