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This pilot study explores how individuals reason through ill-structured problems with and without the aid of generative AI. As tools like ChatGPT become integrated into daily thinking, they influence how people construct arguments, offload cognitive effort, and justify decisions. Two graduate students each answered one ill-structured question independently and one with AI support. Questions were developed using six design criteria and scored using the AAC&U Critical Thinking VALUE rubric. AI-assisted responses were often more structured but sometimes less reflective and original. Findings highlight how AI may shape not just what we say, but how we think—raising implications for educational design, cognitive delegation, and the evolving nature of critical reasoning in AI-mediated environments.