This article looks across two teacher education programs to review the tensions and benefits of critical, project-based (CPB) clinical experiences. The first study examines a project embedded within a methods course focused on secondary English language arts (ELA) preservice teachers (PSTs) engaging with youth around a shared writing activity. In the second study, PSTs partnered with local high school students to consider the relevance of writing in and out of schools. We consider how CPB clinical experiences served as mediating spaces that address the disconnect between universities, schools, and communities (Zeichner, 2010). Data analysis suggested there are numerous tensions and benefits associated with CPB clinical experiences for PSTs, teacher educators, and school-based teachers and students. We draw on the findings from this study to make recommendations for future iterations of such work.