This paper examines the utility of constructed/extended response questions as a means to promote conceptual understanding of mathematics and facilitation of positive student outcomes. Currently, investigations of item formatting related to facilitating student understanding and achievement in mathematics is limited. Because items that prompt students to construct a response are thought to support conceptual development, we argue that such strategies will enhance knowledge transfer, and in the process, develop students' flexibility in thinking through multiple contexts. Discussion in the paper centers on research supported by the impact of testing on classroom instruction, with special emphasis on how such an impact can be evaluated and used to enhance conceptual learning while eliciting positive outcomes from all formats of testing items. This study uses a multivariate correlational analysis of longitudinal archival test results (grades 3-5) from an urban upstate New York elementary school to describe relationships between CR items and student proficiency.#Mathematics