Which opportunities due to digitization are exploited by criminals? And how do criminals gather the required ICT-expertise to take advantage of these opportunities? This exploratory study provides insight into criminals seeking ICT-expertise by analyzing five Dutch cases. This paper shows that criminals seeking ICT-expertise take advantage of companies and employees in the ICT-sector that act in a gray area. It is noteworthy that the initial contact of criminals seeking ICT-expertise is often immediately directed to criminal collaboration. In these cases, ‘capacity’ is more important than ‘contact’. Furthermore, this paper discusses the role of forums for criminals seeking ICT-expertise. Criminals take advantage of the transfer of knowledge on forums and the existence of crimeware-as-a-service. Finally, this study falsifies the statement that there is a clear division between traditional offender groups taking advantage of the possibilities arising from ICT, and crime groups operating exclusively online. In practice, there are many connections between online and offline activities.