This is the first study to explore how cryptomarket actors are increasingly adopting encrypted messaging applications to “direct deal” beyond the provided platforms, to obviate the protocols of cryptomarkets, and to diversify the communication experience of drug buying via the dark net. Drawing on 965 forum posts discussing encrypted messaging applications, results showed that direct dealing may be more likely to occur in the context of preestablished trust between vendors and buyers, during instances of law enforcement crackdowns, and when buyers are enticed by discounts or promotions. Our findings also suggested a general hesitancy toward direct dealing, as it was often associated with greater exposure to scams, and perceptions that direct dealing increases the risks concerning personal security and detection from law enforcement. These findings provide insight into the interconnection of online drug markets, and how actors make decisions to drift between multichannel supply points mediated by perceptions of trust and risk.