Guide

Zip and unzip files with Claude or ChatGPT, safely

Zip files are still how documents travel. Desktop Steward lets the AI create and open them inside the folders you chose, and it refuses the two things that make archives dangerous: files that try to escape their folder and programs that try to run.

Pack

Zip everything in Documents/AI Workspace/Reports into reports-october.zip in Downloads.

Packed 14 files (6.2 MB) into Downloads/reports-october.zip.

Ask for only certain files (“only the PDFs”), or to leave out a sub-folder.

Unpack

Unpack the archive I just downloaded into its own folder and tell me what is inside.

Unpacked Downloads/contract-pack.zip into Downloads/contract-pack: 3 PDFs and 2 images. One entry, run-me.exe, was skipped because it is a program.

Archives can contain paths like ../../Library/… that would write files outside the folder. Desktop Steward refuses those (“zip-slip” protection) and, in the default mode, skips programs and scripts instead of extracting them.

Undo applies here too

Unpacking is recorded like any other change: “undo” removes the extracted files again. Zipping never deletes the originals unless you ask, and then the confirmation window asks first.

Questions

Does it open password-protected or .rar archives?

Not yet: zip only, without passwords. Other formats are on the list.

Can it zip files from a folder it may only read?

Yes, reading is enough for packing; the zip itself is written into a folder the AI may change.

Try it with Desktop Steward

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

Download for Mac or Windows