In this study, the authors examined the impact of task assignment on the effectiveness of a Web-based experiential exercise based on cognitive flexibility theory to enlighten learner attitudes toward the ill-structured topic of sexual harassment. In the research study, we sought to shed light on the use of a cognitive flexibility approach when measuring attitude changes. Specifically, in this study, we examined whether a learning task assigned to the learner impacts his or her attitude toward the emotionally charged and complex topic of sexual harassment. Results suggest a task need to be carefully constructed so that learners may adapt their attitudes toward sexual harassment.