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This thesis reports on two studies. Study 1 aimed to add value to an underrepresented area of expert-novice research, legal higher education, through a comparison of legal academic experts with tertiary student novices. This study examined the question: what are the key differences in the ways that legal novices and legal academic experts think about and use legal concepts? Verbal protocol method compared first-year tertiary legal students and legal academic experts in their comparison of judgments across two legal cases, responses to questions, and a problem-solving transfer task. A key finding included legal academic experts generally provided more conceptually based and detailed responses than the novices in their case comparisons. Study 2 examined the question: Do learning designs that implement aspects of Analogical Encoding and Productive Failure theory within hypermedia technology learning environments influence novice depth of learning about legal concepts and their ability to apply and use this conceptual knowledge in new problems? This study applied elements of the first study to a hypermedia tutorial. Legal novice participants were enrolled into one of four tutorials, each designed using four distinct learning designs. No statistically significant differences were found across the mean results of the groups in an initial legal case analysis activity. However, the transfer advisory task revealed Hybrid Productive Failure participants scoring significantly higher than Direct Instruction participants. These higher performing participants were generally able to provide conceptual responses reflective of those of experts in study 1. The results support a potential for enhanced learning outcomes where learning activities are sequenced by ‘low structured’ minimally guided approaches prior to ‘high structured’ didactic teaching approaches.