Using hermeneutics as a tool to situate swarm activity within social contexts, this chapter presents a framework and methodology for understanding human interpretation of and interaction with thinking swarms. It reviews contemporary scholarship on the social ontology of technology and emerging research on applying hermeneutics to swarm activity. Hermeneutics allows for evaluating decision-makers’ ability to interpret swarm behaviour in complex security contexts. Case studies of drone and swarm activities illustrate the interface between autonomous systems and society, highlighting interpretive challenges. The chapter proposes using scenario-based simulations to immerse stakeholders in hermeneutics and decision-making processes. Organised into four sections, the chapter introduces hermeneutics, applies it to drone studies, reviews scenarios posing interpretation dilemmas and discusses developing scenario-based simulations to explore hermeneutic frameworks in future swarm scenarios. This approach aims to enhance understanding of how human decision-makers observe, contextualise and interpret drone swarm behaviour, offering insights for security operators, analysts and governance decision-makers.