This dissertation examines the problem-solving processes of seven graduate student novices enrolled in a course in educational assessment and ten educational assessment experts. Using Jonassen's (1997) ill- and well-structured problem-solving frameworks, I analyze think-aloud protocols of experts and novices as they examine ill-structured cases of children with possible literacy difficulties and associated challenges and interviewed participants to elicit their understanding of their problem-solving processes. Three studies make up this dissertation: The first compares the processes of educational assessment specialists as they examine clinical cases to what is known in the literature about medical professionals' clinical problem solving. Unlike medical professionals, these experts used a well-structured problem-solving process to think through the ill-structured cases. The second study compares the experts' and novices' processes before the novices' educational assessment course. While experts used a well-structured problem-solving framework, novices used an ill-structured problem-solving framework. Experts came to conclusions more quickly using their established schema, but novices' comments on the child's strengths and weaknesses and their treatment recommendations were more specific than the experts'. The third study focused on changes in the novices' processes following their educational assessment course. Post-course, four novices considered the second case as they had pre-course, while three novices used a more expert-like process. Though all novices gave detailed explanations of the child's skills and provided specific treatment recommendations, even expert-like novices did not have well-developed schema: they omitted information and were not as efficient as the experts at thinking through the case. These findings have implications for research into how experts and novices might inform one another during problem-solving processes and for how we generally understand the purpose of assessment. Since there were benefits of both the experts' and novices' problem solving approaches, research should explore if and how mentoring partnerships could help novices learn while helping experts retain the comparative benefits of being a novice. However, both groups had weaknesses in their processes; therefore, resulting diagnostic labels should not be considered permanent, and treatment options should not be viewed as ironclad rules. Assessment results should simply be used as launching pad to explore instructional options for a child. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]