Many in the academe and industry have long found computer- Aided design (CAD) education lacking. These critics have decried the lack of strategic skills and the focus on declarative knowledge associated with specific CAD packages. This work will discuss the most recent findings of a three year iterative investigation examining the role of contextual exercises on CAD modeling procedure and the manifestation of adaptive expertise. The effects of a varying number of contextual exercises incorporated in regular instruction throughout a semester will be examined. Contextual exercises consist of students modeling a component that they have a personal connection to, as opposed to a stylized example from the textbook. Modeling performance on a standard assessment is compared for the various groups as is performance on an end of the semester exercise. This work compares the results of student performance on the standard assessment based on whether students received no, one, or four contextual exercises prior to the assessment. Student performance on an end of the semester exercise that is either stylized or contextual in nature is also examined. Student interviews and coding are used to examine the manifestation of adaptive expertise among those various groups. Statistical analyses are used to evaluate differences among the groups. Interview data showed that there was a slightly greater manifestation of behaviors associated with adaptive expertise in the single contextual self-guided exercise group as compared to those students that used a stylized self-guided exercise. However these differences were of limited statistical significance. The implementation of four contextual exercises showed no increase in the manifestation of adaptive expertise behaviors. In both cases, the implementation of contextual exercises did not result in improved performance on the standard assessment. Limitations of the work and possible causes for some of the unexpected results are detailed. © American Society for Engineering Education, 2014.