This article examines the emergence of a dialogue among urban youth about their educational condition, and the opportunities for learning and collaboration that ensue. The study is based on observations and interviews with eight students in a community-based program that supports the engagement of young people in school reform. Notably, the membership includes youth enrolled in both urban and suburban high schools. Findings reveal that the students capitalized on their dialogic inquiry process by constructing knowledge of educational disparity and forging coalitions across district lines. Implications include the possibilities for structuring and supporting students’ social inquiry, and the potential for diverse, student-led dialogues to advance the cause of educational equality.