This report analyzes and evaluates the court-watching program that is a component of the Chicago Appleseed Center for Fair Courts. The Cook County Court System is rife with racial bias, and disproportionately sets up low income and non-white people to fail. The practice of court-watching as a tool of participatory defense presents the opportunity to intervene in a system that works to uphold inequitable distributions of power. Chicago Appleseed represents one possible model, and this paper analyzes that model against other prominent court-watching programs. Through textual analysis and consultation with subject matter experts, this report both explores how court-watching functions within the scope of the broader legal system and lays out a series of recommendations for possible future directions that Chicago Appleseed could take in their own program.