Workshop pedagogy is a staple of writing classrooms at all levels. However, little research has explored the pedagogical moves that can address longstanding critiques of writing workshop, nor the sorts of rhetorical challenges that teachers and students in secondary classrooms can tackle through workshops. This article documents and analyzes the work that two high school educators do to organize a writing workshop around the writing and performance of spoken word poetry. Through a qualitative case study of a four-week spoken word poetry unit, we present features of the unit that both align with tenets of traditional workshop pedagogy and focus that pedagogy on the social and cultural situatedness of literacy. We show that the teachers in this case organized the classroom as a strong discursive community (Matusov, 2007) characterized by collective engagement with a genre, anticipation of a real audience, and renegotiation of classroom authority. We then analyze two discussions that arose during the unit in order to explore how students and teachers grappled with key dilemmas at the heart of writing well: how to shape one's text and message for an authentic audience, and what role(s) teachers and peers should play in students' writing. The analysis suggests that engagement with critical literacy practices like spoken word poetry can leverage writing workshop in ways that highlight the cultural and political dimensions of literacy pedagogy. We conclude by discussing how the communicative dilemmas that arose in this classroom relate to common goals of literacy curriculum, teaching, and research more broadly.