In the realm of cybercrime, technologies that facilitate illicit activities also produce uncertainties based on the hybridity between digital communication and offline presence. Social media platforms have blurred the lines between types of drug sellers, bringing the recreational and the commercial into the same marketplace. In the Nordic data used in this paper, 52 text-based qualitative interviews with recreational and commercial sellers are analyzed via process and variance analysis to identify the relationship between cognitive strategies and seller positions. We ask how sellers’ decision-making processes differ and intersect. Theoretically, we use cognitive sociology to enrich understanding of culture, trust, and rational decision-making in this context. Our findings reveal that recreational sellers often adopt a low-risk, low-gain strategy rooted in cognitive biases, reflecting the recreational nature of their engagement. In contrast, commercially competent sellers employ more complex cognitive strategies, including gut feelings, thus adjusting their decisions with less reliance on initial assessments, leading to a more calculated approach with higher risk tolerance. We conclude with a discussion of intervention strategies; here, we argue for the need for a dual strategy that targets and capitalizes on the differences in cognitive biases in an effective way that poses less harm to recreational sellers.