I tested Cowork on my Downloads - PDFs folder with about 300 files. I asked it to propose renames for generic files and suggest categories before moving anything. After review, I let it rename files and create category folders based on content, then remove numbering prefixes.
📁 File Management Community
Downloads PDF Content Organization
Categorize and rename about 300 downloaded PDFs by content and build a new folder structure
★★☆ Intermediate 30-60 min January 16, 2026
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Scenario
I have hundreds of PDFs in Downloads with messy names and want them categorized and renamed by content.
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Prompt
Review the PDFs in this folder. - Propose clean file names for generic files - Suggest content-based categories - Do not move files until I approve the categories - After approval, rename and create folders (no '/' in names)
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Expected Result
Claude proposed renames and categories first, then created content-based folders and batch-renamed files after approval.
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Tips
- • Test on a copy folder first
- • Ask for a before/after rename report
- • Require a category proposal before execution