Much has been written on the ways in which the Internet benefits opposition movements, in particular in authoritarian regimes. And while some acknowledge that the Internet also provides opportunities for authoritarian governments as well, few have looked at the Internet and social media as a space for back-and-forth actions between the sides. In Azerbaijan, social media allows both the ruling regime and oppositionists to engage with each other and Azerbaijani citizens in new ways. Social media provides the regime with an alternative medium to harass the opposition and demonstrate its power to the citizenry. And while there is a social media presence, the traditional opposition parties do not leverage all affordances of it, however oppositionists not affiliated with traditional parties are leveraging social media to build audiences and engage in action. While the regime is currently “winning” the social media battle through the use of its resources, the new and creative ways that oppositionists are using social media for connective action could prove to be a successful means of dissent.