In this chapter, we examine the relationship between open pedagogical practices and critical information literacy and how they intersect when Wikipedia is introduced in the classroom. Specifically, we discuss the collaboration between a librarian and a course instructor on iterations of Wikipedia assignments across three years and two classes. We unpack the importance of existing infrastructures, such as edit-a-thons and the WikiEdu dashboard, to support bringing Wikipedia assignments into the classroom. We also explore how we worked to connect course content to the renewable assignments and brought larger discussions of representation and community on Wikipedia into the classroom and assignments. Finally, we outline the lessons we learned through this collaboration. In sum, scaffolded projects allowed students to practice their contributions to Wikipedia in a supportive space and fostered critical engagement with course content. In their end-of-semester reflections, students stated that contributing to Wikipedia felt more meaningful and elicited feelings of pride that traditional, disposable assessments did not. They saw themselves as knowledge creators and scholarship creation as part of an ongoing conversation rather than an “end product.” By engaging in peer-review assignments, participating in edit-a-thons, and discussing the assignments with librarians who were not their professors, students also saw their work as part of a broader academic conversation. Through Wikipedia assignments, students can appreciate their own information privilege in terms of access to costly resources and become proactive in sharing that knowledge and their own growing expertise with a wider public.