Claude Cowork deleted my files — can I get them back?

The first ten minutes: Mac-level recovery

Most “Claude Cowork deleted my files” situations are recoverable from somewhere the operating system already keeps around. Work through this list in order and stop at the first one that returns your files.

• Trash. Open Finder → Trash. Sort by Date Added. Anything Cowork removed in the last few minutes is usually here. Right-click → Put Back returns the file to its original location.
• Finder Recents. Cmd-click the Finder icon → Recents in the sidebar. If a file was open in any app today, the path it lived at often appears here even after the file is gone — useful for tracing what was lost.
• iCloud Drive — Recently Deleted. If the folder sits inside ~/Library/Mobile Documents/ (anywhere under Desktop, Documents, or an iCloud-synced folder), open iCloud.com → Drive → Recently Deleted in the sidebar. Apple keeps deleted iCloud items here for 30 days.
• Dropbox / Google Drive / OneDrive version history. If the folder was synced, open the web app for that service. All three keep deleted-file history and per-file version history for at least 30 days on free tiers, longer on paid.
• Time Machine. If you have a Time Machine drive connected, open the Finder window for the parent folder and choose Enter Time Machine from the menu-bar icon. Step back to a moment before the deletion and restore.

If CoworkRestore was already watching this folder

This is the easy path. CoworkRestore takes a save point before and after every Cowork task, so a snapshot from before the deletion almost certainly exists.

1. Open CoworkRestore from the Mac menu bar and select the project folder the deletion happened in. You’ll see its snapshot history, newest at the top.
2. Find the snapshot from just before the deletion. Each row is tagged: claude for Cowork-driven save points, auto for the filesystem watcher, and manual for ones you took yourself. The snapshot you want is usually the most recent claude tag whose timestamp is just before the task that deleted things.
3. Open the snapshot to see the changed-files list. Anything Cowork removed shows up as deleted. You can scan the list to confirm what’s missing before restoring anything.
4. Restore. You have two options:
   • Per-file restore brings back only the files you actually lost — useful if Cowork also made edits you want to keep.
   • Restore the whole snapshot rewinds the entire folder to that point in time — the right move if Cowork deleted broadly and you don’t want to cherry-pick.
5. If the restore wasn’t right, undo it. Every whole-snapshot restore takes a safety snapshot first. Undo last restore reverses it — available until the next snapshot lands on top.

For the full file-by-file workflow — including how to read the before/after view and which tag to look for in mixed sessions — see how to undo bad file changes from a Cowork session.

If you did not have snapshots yet

Honest answer: no snapshot tool can recover what wasn’t being watched. CoworkRestore can’t help with deletions that happened before you installed it or before you added this folder. What you do have is the Mac itself.

• Trash — carefully. If you’ve already emptied it, stop writing to the disk until you’ve checked the other options. New writes are what make Trash-emptied files unrecoverable.
• Time Machine, even hourly snapshots. If Time Machine is on but no external drive is attached, macOS still keeps local snapshots on your internal disk for about 24 hours. Open Time Machine from the menu-bar icon — you may see entries even without a backup drive.
• Cloud version history is your best friend if the folder was synced. Dropbox, Google Drive, OneDrive, and iCloud all let you restore deleted files and earlier versions from the web app.
• Email and Slack attachments. If you’ve ever sent a copy of the file, the attachment is a recovery path. Spotlight search the filename across Mail and any messenger.
• Don’t install file-recovery utilities yet. Many write to the same disk as part of their installer, which can overwrite the very sectors you’re trying to recover. If you’re going down that path, install onto an external drive.

Once you’ve recovered what you can — or accepted the loss — set up the safety net so the next time isn’t this hard. Start with the pre-flight checklist for any Cowork task that touches a folder you care about.

The iCloud “Optimize Storage” trap

Worth knowing because it’s a documented gotcha for any AI tool touching an iCloud Drive folder. With Optimize Mac Storage on, macOS evicts local copies of files you haven’t opened recently and replaces them with placeholder stubs. The stub is a 0-byte file with the right name — opening it in Finder triggers a download.

A tool that walks the filesystem the way an AI agent does won’t always trigger that download. It can read the stub as an empty file, copy the empty version somewhere, and then delete the “original.” The end state is empty copies and no originals. Two ways to avoid it:

• Turn off Optimize Mac Storage for the working folder. System Settings → Apple ID → iCloud → iCloud Drive → uncheck Optimize Mac Storage. Your files will be fully downloaded again over the next minutes or hours.
• Or work in a folder that is not inside iCloud Drive. A project folder under ~/Projects or ~/Work is the simplest fix. CoworkRestore is happy with any local path.

If the bigger problem is that Cowork emptied an entire project, the sibling guide Claude deleted my project — how do I get it back? covers the broader cross-tool recovery path. If you’re ready to make sure this never happens again, the pre-flight checklist is the place to start.