Information security practitioners and researchers who possess sufficient depth of conceptual understanding to reconstitute systems after attacks or adapt information security concepts to novel situations are in short supply. Education of new information security professionals with sufficient conceptual depth is one method by which this shortage can be reduced. This study reports research that instructed two groups of ten undergraduate, pre-cryptography students majoring in Computer Science in cryptography concepts using representational understanding first and representational fluency first instructional treatment methods. This study compared learning results between the treatment groups using traditional paper-based measures of cognitions and fMRI scans of brain activity during cryptography problem solving. Analysis found no statistical difference in measures of cognitions or in cognitive processing, but did build a statistical model describing the relationships between explanatory variables and cryptography learning, and found common areas of cognitive processing of cryptography among the study's twenty subjects. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]