In this presentation we will describe a research programme that uses CADS as an interdisciplinary methodology in order to explore one of the most widely debated and complex questions of our digital society: how do individuals and groups seek to generate trust in digital environments? Two case studies are selected to this end. The first is selling and buying drugs in the Dark Net, specifically in the flagship crypto-drug market Silk Road. The second is promoting extreme far-right values via Facebook and Twitter by the groups Reclaim Australia and Britain First. Whilst clearly different in terms of the activities performed and the digital platforms used, both case studies centrally involve attempts at generating trust discursively. In crypto-drug markets, users seek to enhance their reputation within a highly competitive, extra-judicial environment by, for instance, offering advice about avoiding being scammed by other users. Similarly, the extreme far right groups Britain First and Reclaim Australia use social media posts to mobilise a range of themes across domains as varied as food certification and vaccines in order to inculcate and create a sense of trustworthiness in their values, while delegitimising those of their perceived enemies. In addition to presenting the key results of our case studies, our talk will include a (self-) critical reflection of what working with digital corpora entails from a technical and analytic perspective. Language data from digital environments are tied to the ‘structure’ of the platform through which they are published on the web. Creating a corpus of such data involves understanding this structure, which differs from platform to platform and which has a direct influence on both how the corpus tools can be used and on the language analysis itself. Through our case studies, we will reflect on how corpus linguistics methodologies may overcome the complexities of digital datasets as well as the current limitations faced. Finally, our presentation will reflect upon the challenges and opportunities of integrating CADS methods and policy-making and law enforcement practical needs.