Guide

Free up disk space with Claude or ChatGPT, without deleting the wrong thing

The scary part of cleaning a disk is deleting the wrong file. Desktop Steward lets the AI measure, propose and delete, but every deletion opens a window on your computer first, and everything can be undone for 7 days.

Step 1: measure

What takes the most space in my Downloads, Documents and Pictures?

Downloads: 18.4 GB, mostly installers (.dmg, .exe) from 2024 and video files. Pictures: 41 GB, 2.3 GB of them identical duplicates. Documents: 3.1 GB. The ten largest files: …

Ask follow-ups: “which installers are older than a year?”, “videos larger than 500 MB”, “duplicate photos”.

Step 2: delete with a net under you

Delete the installers older than a year and the duplicate photos you found.

A window opens on your computer: “Delete 23 items? setup-2024.dmg, … Kept for 7 days and can be undone.” Click Allow.

Deleted files go to Desktop Steward's holding area, not straight to the Trash. They count as freed only after 7 days, when they are removed for good. Say “empty the holding area now” if you need the space immediately.

What the AI will not touch

  • Anything outside the folders you opened: no system folders, no Library, no application data.
  • Passwords, keys, browser profiles and mail, even inside an opened folder.
  • Programs and installers it is asked to open; it may delete them, never run them.

Questions

Can it clean the whole disk, caches and system files?

No, and on purpose. It works inside the folders you opened. For caches use your system's own storage tools.

Does undo bring back deleted files exactly?

Yes, to the same path, for 7 days (configurable). After that they are gone.

Try it with Desktop Steward

Free on Mac and Windows. Asks before anything risky, undo for every change.

Download for Mac or Windows