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From 2011-2014, a state conducted research-based transition-focused community conversations in 20 ISDs representing 504 LEAs. Conversations focused on answering: (1) are schools preparing students to belong and succeed in their community, (2) are communities prepared to support students once they leave school, and (3) how do we know? The study included a representative sample of diverse stakeholders that represented education, agencies, business, families, and students. Each conversation included four or more observer-note takers. Thematic analysis showed across group strengths of strong interagency cash transfer agreements and structures for community-based programming. Reported challenges included: data collection and use, balancing academic requirements and transition education, clarifying graduation requirements, and training and involvement of families in the transition process.