Civil society leaders develop relationships with officials and engage in contentious politics. Some resort to destructive tactics like arson and assault to target the officials they work with. Why do civil society leaders use destructive protest tactics? This article argues that leaders use destructive tactics when both they and officials need clear information and when leaders believe that officials will offer lucrative agreements to stop destructive protests. The research suggests that this dynamic is more likely in weakly institutionalized, highly politicized, and resource-strapped environments. The research supports the argument by process-tracing cases of peaceful and destructive protest by street vendor organizations and officials’ responses in El Alto, Bolivia. The argument and cases suggest that civil society leaders are more likely to target women and other minoritized people because leaders are more likely to underestimate minoritized officials, but that these officials are then more likely to punish the perpetrators.