Sort and rename thousands of personal files with approval at every step

After losing twenty-three minutes hunting for one holiday photo, Dubowsky opened Claude Code in the Claude desktop app and gave it the whole home folder, every document, photo and download. The job went in four steps. First it had to look and report without moving anything. Then it proposed at most six folders, named the way Dubowsky would say them out loud, and showed which files would go where. Then it suggested new file names that start with the date and say what the file is, listing old and new names side by side. Nothing moved or got renamed until Dubowsky approved. New files now go to it on Fridays to be filed into the same folders.

The survey took about two minutes. Most of the 9,412 files were fine; the mess sat in the desktop, Documents and a Misc folder, 312 files in all. Those went into Letters, Money, House, Photos, Travel and a Not Sure folder for anything it could not place. Duplicate photos were removed after approval. The whole job took one afternoon, mostly spent reading the plan and arguing over names. Two weeks on, Not Sure still holds 41 unsorted items, and the weekly top-up takes about a minute.

Dubowsky ignored Anthropic's advice to give it one dedicated folder; it could see the tax returns folder and only a sentence in the prompt kept it out. The backup was checked first. It sorts by what a file is, not by whether it matters. Large folders eat into plan usage and the app must stay open. Left alone it proposed far more folders than wanted, so cap the number.