Ignored in the finalized Master Settlement Agreement (National Association of Attorneys General, 1998), the unmonitored, unregulated World Wide Web (Web) can operate as a major vehicle for delivering pro-tobacco messages, images, and products to millions of young consumers. A content analysis of 318 randomly sampled pro-tobacco Web sites revealed that tobacco has a pervasive presence on the Web, especially on e-commerce sites and sites featuring hobbies, recreation, and "fetishes." Products can be ordered online on nearly 50% of the sites, but only 23% of the sites included underage verification. Further, only 11% of these sites contain health warnings. Instead, pro-tobacco sites frequently associate smoking with "glamorous" and "alternative" lifestyles, and with images of young males and young (thin, attractive) females. Finally, many of the Web sites offered interactive site features that are potentially appealing to young Web users. Recommendations for future research and counterstrategies are discussed.