This article investigates the critical thinking difficulties of finance majors when asked to address ill-structured finance problems. The authors build on previous research in which they asked students to analyze an ill-structured investment problem and recommend a course of action. The results revealed numerous critical thinking weaknesses, including a failure to address the client's problem, use analytical tools systematically, construct rhetorically useful graphics, or translate finance concepts and methodologies into lay language. The present research aims to understand more deeply why students struggle with ill-structured problems. Using think-aloud protocols, audiotaped interviews, and other strategies, the authors explore causes of finance students' difficulties and suggest strategies for addressing them. The results suggest that the homework tasks typically given them, such as quantitative problem sets using algorithmic procedures, do not prepare them to confront ill-structured problems requiring disciplinary arguments aimed at specified audiences. Research further suggests that teaching audience adaptation--especially for nonexpert audiences--is helpful in promoting critical thinking.