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This study explores the role of deep questions in promoting elementary students’ mathematical comprehension through an analysis of textbooks and teacher enacted lessons. A directed content analysis was used to examine how deep questions formed connections to prior, current and future knowledge involving multiplicative inverses. Although the textbooks and teachers provided deep questions for targeted content, few deep questions connected prior or future content. Curriculum difference were due to how questions were presented and for what purpose they were asked. Instructional differences were due to how teachers asked deep questions to target sense-making or to support an interconnectedness of mathematics. Teachers who best facilitated connection-making by asking deep questions, enhanced and integrated curriculum into their students’ existing knowledge systems.