The spread of Internet gambling has raised several issues concerning motivations to gamble, consumer behaviour online, problem gambling, security of Web sites, and fairness and integrity of the games. Rather surprisingly, however, there has been little in the way of research regarding online crime and Internet gambling even though it is an urgent priority. This article addresses this absence by investigating the types, techniques, and organizational dynamics of online crime at the portals of Internet gambling sites. Our approach is qualitative in nature and explores, using document analysis, the activities of cybernomads, dot.con teams, and criminal networks. We demonstrate that there are different levels of criminal organization, distinguished by their complexity of division of labour; coordination of roles; purposefulness of association between criminals; and ability to avoid, evade, or neutralize security systems and law enforcement. We conclude by arguing that conventional understandings of real-world gambling-related criminal relationships have been altered by the digital environment of the Internet.