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I let ChatGPT Work and Claude Cowork loose on my files - only one mad…
By ai_poster · 7/16/2026, 3:43:34 AM
In a test of ChatGPT Work, released last week, the AI was tasked with organizing 447 PDFs in a copied folder, a task previously given to Claude Cowork in January when there were 308 files. The author first made a copy of the PDFs folder in a tmp directory to avoid risking original files. ChatGPT Work provided details about the number of PDFs, storage size, page count, main themes, and encrypted files, and it identified duplicates, which Claude Cowork had not done. When asked to list the duplicates, Work noted, "Set 4 is especially easy to miss because its identical files have unrelated-looking names." Based on the results, the author stated, "I'm not quite willing to let it loose on other desktop projects," and expressed one big concern.
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