As computer-aided design (CAD) tools become more integral in the product commercialization process, ensuring that students have efficient and innovative expertise necessary to adapt becomes more important. This work examines the role of adaptive expertise on CAD modeling behavior and the effect of contextual modeling exercises on the manifestation of behaviors associated with adaptive expertise in a population of student participants. A methodology comprising multiple data elicitation tools is used to examine these relationships; these tools include: survey data, model screen capture data analysis, and interviews. Results show that participants engaged in contextual exercises spent more of their modeling time engaged in actual modeling activities as opposed to planning when compared to a control group. Limited statistical support is provided for the role of contextual exercises leading to the manifestation of behaviors associated with adaptive expertise. The amount of time spent engaged in actual modeling is positively correlated with the adaptive expertise behaviors identified in the interviews. © 2013 Springer-Verlag.