Why do people use anonymity-granting technologies when surfing the Internet? Anecdotal evidence suggests that people often resort to using online anonymity services, like the Tor network, because they are concerned about the possibility of their government infringing their civil and political rights, especially in highly repressive regimes. This claim has yet to be subject to rigorous cross-national, over time testing. In this article, econometric analysis of newly compiled data on Tor network usage from 2011 to 2013 shows that the relationship between political repression and the use of the Tor network is U-shaped. Political repression drives usage of Tor the most in both highly repressive and highly liberal contexts. The shape of this relationship plausibly emerges as a function of people’s opportunity to use Tor and their need to use anonymity-granting technologies to express their basic political rights in highly repressive regimes.