The spread of the Internet coupled with knowledgeable users has led to the use of digital media as a tool for advocacy and activism. Building on theoretical foundations of eventful histories (Sewell, 2005) and Digital Formations (Latham & Sassen, 2005), this paper outlines a framework for understanding the interrelated nature of contentious politics and new technological developments. The goal of this article is to develop a theoretical explanation of evolution of activists’ digital repertoires in response to authorities’ reactions and repressive measures, through studying three interrelated cases. This work builds on existing research by investigating the use of the Internet in contentious politics in Iran since the beginning of the 21st century and analyzes the ongoing tension between activists and authority forces. This analysis documents changing digital repertoires of contention in the context of messaging, blogging, and social networking sites in Iran and offers a framework for better understanding the use of the Internet in contentious politics.