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The online sourcing, supply, and purchase of illicit drugs is fast transforming drug markets worldwide. Although the long-term development of simple communications technology over time (from pagers to mobile phones) continues to impact and extend local drug supply dynamics, it is the recent developments of dark web cryptomarkets, social media applications (like Instagram), encrypted messaging applications (like WhatsApp), and surface web platforms, such as LeafedOut, that are changing the drug supply landscape online. The use of technology in drug supply has tended to go hand in hand with improving the efficiency of supply and opportunities to reduce exchange-related risks for both buyers and sellers. In relation to app-mediated supply, for example, the use of encrypted messaging provides enhanced security for arranging purchases beyond the lurking surveillance of law enforcement. Despite the perception of improved safety, however, the use of social media apps and other online platforms can expose both buyers and sellers to risk scenarios they may not fully appreciate. Drawing on two recent studies on the use of social media apps and the online platform LeafedOut as mediators of drugs supply, this chapter will consider how these mid-range (between cryptomarkets and traditional telecommunications such as basic texting/calling and material ‘street’ markets) virtual spaces are being utilised for drug supply and the extent to which this is ‘just more of the same’ or provides new structures and experiences for those engaging with it and in what ways. Consideration will also be given to contradictions in the mid-range market space where the broad perception of reduced risk from the use of encrypted messaging can in fact produce greater levels of risk for some buyers and sellers depending on how they engage with the process/es.