Wikipedia's gender gaps are both well-established and well-challenged, and while Wikipedia-based assignments have become more common in composition, teacher-scholars have not fully explored the opportunities for feminist pedagogy offered by the encyclopedia. This article reports on a teacher research study designed to examine the efficacy of the feminist rhetorical approach for understanding critical literacy learning through Wikipedia-based assignments in First-Year Composition (FYC). Findings from student forum posts, surveys, and reflection essays suggest that, despite its benefits, the Wikipedia assignment has been met with challenges that hinder students from making contributions critically and effectively, especially as they struggle to assume agency and criticality in the FYC classroom. By identifying and addressing these challenges, we seek to offer alternative approaches to teaching feminist rhetorical inquiries in FYC, and to expand the current critical practices in Wikipedia-based writing instruction.