The development of critical thinking is crucial in professional education to augment the capabilities of pre-professional students. One method for enhancing critical thinking is participation in role-playing simulation-based scenarios where students work together to resolve a potentially real situation. In this study, undergraduate nursing students were divided into small groups (2-3) to role-play a medical emergency (stroke) within a high fidelity simulation environment. The research team utilized a cross-case comparison design; cases were defined by the different roles played by the nursing students (e.g., primary nurse, secondary nurse, and family member). Results indicated that although students in all three roles displayed instances of reflection, contextual perspective, and logical reasoning, these were not distributed evenly across roles, with family members demonstrating fewer instances of reflection and logical reasoning and secondary nurses demonstrating fewer instances of contextual perspective. However, evidence of students' abilities to apply clinical standards was observed fairly equally across all three roles. Implications for the use of role-plays within high-fidelity simulations are discussed.