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What accounts for variations in protests against authoritarian governments? This article focuses on the interactive relationship between the proliferation of information and communication technologies (ICTs) and the opening of political opportunity structures. This paper suggests that ICTs’ effects on protests are likely ambiguous due to the tensions that exist between the protest-facilitating and protest-hindering aspects of ICTs. As political opportunity structures become more open, however, the diffusion of ICTs is expected to have a more significant and positive impact on protests. Negative binomial regression tests based on a dataset of 103 authoritarian countries (1990–2017) show inconsistent evidence for the claim that the diffusion of ICTs in itself is a significant and positive determinant of protests. As hypothesized, ICTs are found to affect protests significantly more positively with the opening of political opportunity structures—that is, when national elections are held openly and competitively, and the state enforces less restrictions on political participation. By demonstrating how the influence of ICTs’ diffusion on protests varies according to these moderating factors, this article connects and applies the relational resources and political opportunity approaches from the social movement literature to the study of protesting authoritarianism.