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This longitudinal study focused on different AI tools' ability to use the Task Analysis Guide (TAG; Stein \\& Smith, 1998) to classify the cognitive demand of mathematics tasks. In particular, it examined whether this classification ability changed with (1) model version updates over time and (2) few-shot prompting using exemplar tasks. We tested a general-purpose AI tool (Gemini) and an education-specific AI tool (Coteach). The specific tools were selected because of their relatively high performance on relevant published benchmarks and prior task-specific tests. Models were tested at baseline, retested with model version updates, and then tested again using few-shot prompting (two exemplar tasks for each cognitive demand category). 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