In the realm of cybercrime, technologies that facilitate illicit activities also produce uncertaintiesbased on the hybridity between digital communication and offline presence. Social media platformshave blurred the lines between types of drug sellers, bringing the recreational and the commercialinto the same marketplace. In the Nordic data used in this paper, 52 text-based qualitative inter-views with recreational and commercial sellers are analyzed via process and variance analysis toidentify the relationship between cognitive strategies and seller positions. We ask how sellers’deci-sion-making processes differ and intersect. Theoretically, we use cognitive sociology to enrichunderstanding of culture, trust, and rational decision-making in this context. Ourfindings revealthat recreational sellers often adopt a low-risk, low-gain strategy rooted in cognitive biases, reflect-ing the recreational nature of their engagement. In contrast, commercially competent sellers employmore complex cognitive strategies, including gut feelings, thus adjusting their decisions with less reli-ance on initial assessments, leading to a more calculated approach with higher risk tolerance. Weconclude with a discussion of intervention strategies; here, we argue for the need for a dual strategythat targets and capitalizes on the differences in cognitive biases in an effective way that poses lessharm to recreational sellers.