The fast changing pace of modern CAD tools has demanded the users to be more adaptive to apply their CAD skills. This paper presents the initial work to transform adaptive expertise in the CAD education. An adaptive expertise survey (AES) and a contextual exercise were implemented in a freshman CAD class. The students' responses to the survey and interviews were analyzed. The CAD models were evaluated based on the attributes. The statistically significant relationships among the variables are reported. The analyses examined the role of adaptive expertise in CAD modeling and the role of learner-centered contextual exercises on CAD modeling procedures. The findings suggest some differences between the students' demographics and their adaptive expertise characteristics and positive effect of the contextual exercise on students' CAD modeling procedures. © 2014 CAD Solutions, LLC.