This chapter explores emerging challenges and future directions such as organised crime on the Internet, cross-border policing, and the resilient and adaptive nature of organised crime, which also operates as an explanation for the persistent nature of the problem in the face of police intervention. Attention is paid to the impact of new technology, including the ease with which it enables crime to be committed across borders, and for electronic communications to be protected with strong encryption that hampers interception. This chapter questions whether an enforcement driven approach is the best social policy to adopt and provides a discussion of possible alternatives to criminalisation and enforcement, including harm minimisation and regulation, which coincides with moves towards decriminalisation and regulation of marijuana and other “illicit” substances around the world.