It is commonly recognized that social media presents vast new opportunities for terrorist groups seeking to radicalize audiences. However, few scholars have studied the actual mechanisms by which radicalizing messages are delivered to those audiences. Within this paper, the author explores one key aspect of the phenomenon of ‘jihadi cool’ – that is, the rendering of pro-Islamic terrorism into something hip and trendy among online audiences. Discussed is the use of political jamming: a subversive, satirical activity that draws on humor to reinforce ideological messages. The opportunity for countering these messages through the same technique is also considered.