This study examines the role of digital media within the Ultra-Orthodox Jewish community in Israel, a conservative closed community, whose leadership is unable or unwilling to control the effects of digital media on the rank-and-file. Over the past decade, digital media have played an important role for challenging authoritarian rule around the globe. Especially in ideological communities sustained by strict taboos, digital media hold the potential to subvert hegemonic discourses. In this study, we make use of an incident that forced Israel’s Ultra-Orthodox community to address its long-standing taboo and hateful attitudes toward LGBT and Queer issues. In July 2015, an Ultra-Orthodox community member attacked participants of the Jerusalem Gay Pride Parade, murdering one and wounding six. While traditional community media attempted to ignore the event, two major Ultra-Orthodox news websites fell outside the control exercised by the community leadership, and enabled subversive discussions within the Ultra-Orthodox community. Through a process of negotiating the meaning of the attack, these discussions resulted in a reframing of the boundaries of the community, breaking a path for further contestation and debate. Using grounded theory analysis, this article contributes to a better understanding of the role of digital media in enabling contestation and challenging established power structures within authoritarian closed communities.