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The everyday lived realities of street-level and small-wholesaling drug dealers involve mediating risks in a technologically saturated world. This paper demonstrates how technologies are innovatively appropriated and their risks mitigated in an on-going evolutionary battle between criminals and the police. The advent of modern technologies generates new opportunities for the commission of organised crime. Technologically savvy cybercriminals and terrorists alike capitalize on the new and evolving avenues available through the internet to further their criminal goals. Accordingly, the use of cybertools for furthering criminal ends has led to a moral panic by policy makers and the media, which has underpinned the legitimizing of unprecedented levels of surveillance and data mining worldwide of both illicit and licit actors. On the street level, mobile technologies that do not require extensive technical expertise to employ, equip drug dealers with additional tools to more efficiently conduct their business. Such technologies can accentuate risks for criminals as enforcement agencies may penetrate their devices and monitor their activities. The association of risk alters the behavior of the user, modifying their criminal activities and policing strategies.