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Sort 2,200 Downloads files into folders with summaries

Cowork grouped a Downloads folder of 2,200 loose files by type and summarized each folder in under 20 minutes, mostly non-destructively.

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Use case overview

Cowork grouped a Downloads folder of 2,200 loose files by type and summarized each folder in under 20 minutes, mostly non-destructively.

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Reported experience

  1. What they did

    Karen Spinner gave Claude Cowork access to her Downloads folder and asked it to group files by type and summarize each group. It inventoried the 2,200 files and proposed 11 folders, and she approved the plan. It then sorted the files, proposed subfolders, and moved old installers and duplicates into review folders. It asked permission before deleting anything. Later it read and renamed vague files.

  2. How it went

    About 20 minutes of interaction left 2,101 files in 11 folders, 67+ files renamed, and 2GB of old installers identified. Rename suggestions were roughly 70% accurate. A commenter said a rollback failed.

  3. Worth knowing

    Back up first. Cowork needs a paid Claude plan, a Mac, and the desktop app left open. Prompt injection is a risk, so keep credentials and sensitive files out of the shared folder.

Example prompts

Try with Claude Cowork
Look through my Downloads folder at [folder path] and propose a plan to group the files into folders by type or topic, with a one-paragraph summary of each folder. Show me the plan first and wait for my approval. Then move files only, never delete anything, and finish with a list of what went where.

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