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Providing contrasting cases to students prior to presenting them with canonical methods can be a helpful and productive learning technique, as demonstrated by Schwartz & Martin (2004), as well as the other speakers in this symposium. One open question has been the role of motivation in these findings; perhaps this style of instruction has unique motivational properties, or perhaps it only provides benefits for students already driven to deeply understand the material. In a series of studies, we have explored the role of student goals in learning from comparing cases in ill-structured learning environments and in more traditional, well-structured environments. Specifically, we have examined how existing student mastery-approach achievement goal orientations for math, assessed using a standard questionnaire (Elliot & Murayama, 2008), affect the ability to transfer from these types of learning activities. These particular goals reflect a student’s desire to develop his/her competence and skill in math. Across two studies with college students (n = 202) learning elementary statistics, we have found evidence that increased mastery-approach orientation predicts increases in knowledge transfer, regardless of type of instruction. More critically to this symposium, a pattern has been observed where the effect of existing mastery-approach orientations is larger for those completing the well-structured, tell-and-practice activity, relative to those completing the ill-structured, comparison-based invention tasks. Instead, for students completing comparison-based invention tasks, there seems to be a stronger momentary increase in mastery-related goals for the task itself, which may dampen the effect of existing mastery-approach orientations in predicting transfer. Additional evidence for this claim comes from questionnaires administered during the learning activities. It appears that invention with contrasting cases drives students to focus more on developing their own understanding, and this may be partly responsible for the observed benefits on transfer. Conversely, learning deeply while being provided a formula to use on those same cases is dependent on existing student motivations to understand. The studies presented here illustrate that discovering by comparing cases may lead to the development of motivation to understand, and that a full account of the benefit from comparing cases should include both cognitive and motivational factors.