© 2015 CAD Solutions, LLC.The authors have implemented a series of contextual CAD modeling exercises in a freshman CAD class to transform adaptive expertise in the CAD education. The students were interviewed before and after the exercises to capture their manifestation of adaptive expertise. At the end of semester, a CAD modeling test was given to the students. The CAD modeling procedures were evaluated based on the model attributes and students’ screen-recordings. The data analyses examine the role of learner-centered contextual exercise in CAD modeling process, and the correlations between the adaptive expertise in CAD modeling procedure. The findings show that the contextual exercises have positive effects on improving students’ adaptive expertise and CAD skills.