Although there has been much interest in how communication technology can shape conflict, the deliberate targeting of the telecommunication infrastructure by rebel groups has been largely overlooked. This article demonstrates that while some rebel groups systematically target telecommunications, others do not. It is argued that this reflects deliberate choices, and that rebel groups adapt their strategies based on cost–benefit analyses. Given the aim of avoiding detection and being targeted themselves, rebels may be more likely to target the telecommunication infrastructure when faced with a government with a technologically sophisticated military. However, a further increase in the opponent’s technological capabilities beyond a certain tipping point may compel rebels to employ preventive measures other than targeting telecommunications. Marxist-socialist or religious groups are expected to be more likely to target telecommunications to maintain a homogeneous propaganda space directed at their constituency, facilitating indoctrination and propaganda. These expectations were evaluated in an analysis of all rebel groups for the period 1970–2013. The results showed a non-linear relationship between rebel targeting of telecommunication infrastructure and the technological capabilities of the government forces, while Marxist-socialist and ethno-religious groups were more likely to target telecommunications compared with other groups.