This chapter explores some of the dilemmas that arise in using uncertainty as a lens to interpret societal problems and issues. Using several cases to open up discussion we argue that it is vitally important to understand the historical, political and cultural context in which debates about risk, uncertainty and (in)security materialise. Arguing for a re-specified, context-specific account, we seek to unravel dominant understandings of uncertainty in three domains: cyber security, counter-radicalisation strategy and mechanisms for coping in the aftermath of structural violence. While acknowledging the value of uncertainty as an heuristic device, we argue that established units of sociological analysis – such as power and ideology – remain important explanatory concepts in understanding institutional actions and policy drivers.