We investigate effects of cognitive style (field dependency) on performance on examination questions that differ in terms of contextual familiarity and degree of structure. We find that field independent students perform significantly better solving unfamiliar questions than do field dependent students, but possess no significant advantage over field dependent students when solving familiar questions, as supported by theory. For unstructured questions, we found no significant performance difference between field dependent and independent students, consistent with the inconclusive nature of current research findings. For structured questions, we found that field independent students performed significantly better than their field dependent counterparts. These results will help educators understand the role of cognitive style on students’ ability to function in unfamiliar settings, which is one of the recommendations of the Accounting Education Change Commission.