This paper reports on two studies. The first study used a verbal protocol method to examine first-year tertiary legal student novices and legal academic experts in their comparison of judgments across two legal cases, responses to questions about the cases, and a problem-solving task. Key findings were that the legal academic experts generally provided more conceptually based and detailed responses than the novices in their case comparisons. The academics performed 43% higher than the novices when asked to identify issues of each case, and 70% higher in their identification of the ratio decidendi of each case. On the problem-solving task, the differences between the two groups was closer, although academics scored 20% higher than the novices. Also reported are the preliminary results of a second study that applied elements of the first study to a tutorial that used a hypermedia learning environment. Key findings of Study 2 relate to participants that engaged in the analysis of the legal cases prior to viewing a video resource. These participants significantly performed better in the transfer task than participants that viewed a video resource prior to the legal case analysis activity. Another significant finding related to the analysis type of legal cases, indicating that asking participants to summarise the key legal points in the judgments of legal cases separately and chronologically produced better transfer results than asking participants to directly compare the key legal points. Implications of this research related to professional legal education and learning design are discussed.