In 2007, the authors conducted a case study of 13 teachers across seven elementary schools. We learned that, due to pressures of the No Child Left Behind Act (NCLB, 2002) and state mandated testing, these schools were akin to reading academies—focused chiefly on the teaching of reading skills. They promised to share their results with local administrators and teachers, initiating the reconsideration of elementary social studies. To this end, they revisited school sites, revealed their findings, and offered to “fit into” ongoing discussions of curricular change. They attempted to engage teachers in courageous conversations, or honest, frank appraisal of current conditions. Eventually, they talked with approximately 100 K-6 teachers, principals, and district administrators. Framing their inquiry in Giddens (1984) theory of structuration, they present their efforts to build collaborative relationships in three cases of narrative inquiry. They follow it with dilemmas and insights for the field organized into five considerations: courageous conversation, curricular control, integration, social studies advocacy, and courting schools.