Censoring nation-states deploy complex network infrastructure to regulate what content citizens can access, and such restrictions to open sharing of information threaten the freedoms of billions of users worldwide, especially marginalized groups. Researchers and censoring regimes have long engaged in a cat-and-mouse game, leading to increasingly sophisticated Internet-scale censorship techniques and methods to evade them. In this dissertation, I study the technology that underpins this Internet censorship: middleboxes (e.g. firewalls). I argue the following thesis: It is possible to automatically discover packet sequence modifications that render deployed censorship middleboxes ineffective across multiple application-layer protocols. To ev...