In this presentation we will describe a research programme that uses Corpus Assisted Discourse Studies (CADS) as an interdisciplinary methodology in order to explore how individuals and groups generate trust in digital environments that operate extra-judicially. Two case studies are selected to this end: selling drugs in the Dark Net and sexually grooming children online. Whilst clearly different in terms of the illegal activities performed, both contexts centrally involve attempts at generating trust discursively. In crypto-drug markets, vendors seek to enhance their reputation within a highly competitive environment by, for instance, offering advice about avoiding being scammed by other users (Lorenzo-Dus and Di Cristofaro 2018). Similarly, sexual groomers of children invest considerable discursive effort in projecting self-identities as trustworthy adults (for they do not necessarily pretend to be minors), who ‘genuinely care’ about the children they prey on (Lorenzo-Dus et al 2016; Chiang and Grant 2018). In addition to presenting the key results of our case studies, our presentation will reflect upon the challenges and opportunities of integrating, on the one hand, methods in CADS and cognitive linguistics with those used in other disciplines (specifically, public policy and machine learning) and, on the other, academic results within stakeholder needs.