Let Claude Cowork tidy a family desktop, and lose 15 years of camera photos until iCloud recovery brings them back
- Posted
- by Nick Davidov (LinkedIn)
- Last checked
- Method:
- How we verify
Evidence: Described by posterThe person describes what happened in words, without screenshots or video.
FailureThe source says the agent did not get the job done.
What went wrong: The agent deleted 15 years of photos; they came back through iCloud's recovery feature, not the agent.
Outcome
Nick Davidov asked Claude Cowork to organise their spouse's desktop. It asked permission to delete temporary Office files, they agreed, and then it said "ooops": while renaming, it had deleted a folder with every photo the spouse had taken on their camera over 15 years. The deletion was done in the terminal, so nothing was in the Trash; iCloud had already synced the new structure, there was no Time Machine backup, and disk recovery tools found nothing. Apple pointed them to iCloud's recovery feature, which keeps removed iCloud Drive files for 30 days, and the photos started coming back. Their advice: don't let these tools near anything hard to repair or not under version control.
Agent
Prompt Recreated prompt
The source didn't share its exact prompt, so we wrote this from what it describes.
Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to. Goal: Tidy up a messy desktop or folder without any risk of losing files. Fill in before running: - The folder to tidy, and nothing outside it: [FOLDER] - The folder structure I want: [STRUCTURE] - Any folders that must never be touched (photos, documents): [PROTECTED] Back up first. Point the agent at one folder, not your whole drive, and don't let it delete anything. If files vanish, check iCloud's Recover Files (iCloud.com, Data Recovery) or your cloud's version history straight away. Rules: - Before anything else, confirm I have a current backup, and stop if I don't. - Only move files; never delete, overwrite or rename folders. - Show me the full plan (from, to) and wait for my OK before moving anything. - Keep a log of every move so it can be undone. - Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify. Output: A move plan for approval, then a log of what moved where. You'll know it worked when: The folder is tidy and every file is still there.
Customize this prompt
Answer these questions and we'll put your answers into the prompt for you. You can leave any of them empty.
Your prompt
Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to. Goal: Tidy up a messy desktop or folder without any risk of losing files. Fill in before running: - The folder to tidy, and nothing outside it: [FOLDER] - The folder structure I want: [STRUCTURE] - Any folders that must never be touched (photos, documents): [PROTECTED] Back up first. Point the agent at one folder, not your whole drive, and don't let it delete anything. If files vanish, check iCloud's Recover Files (iCloud.com, Data Recovery) or your cloud's version history straight away. Rules: - Before anything else, confirm I have a current backup, and stop if I don't. - Only move files; never delete, overwrite or rename folders. - Show me the full plan (from, to) and wait for my OK before moving anything. - Keep a log of every move so it can be undone. - Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify. Output: A move plan for approval, then a log of what moved where. You'll know it worked when: The folder is tidy and every file is still there.
Scroll to see the whole prompt. Your answers show in green.
3 blanks are still empty: The folder to tidy, and nothing outside it; The folder structure I want; Any folders that must never be touched (photos, documents). They'll stay in brackets in your prompt, so the chat tool may ask you about them.
What you type stays in this browser tab. We don't send it or save it, and it's gone when you leave the page. If you use a "Try this in" button, your answers go to that tool as part of the prompt.
Try this in:
This prompt has blanks to fill in, like [FOLDER]. We'll copy it instead of filling it in, so you can edit it before you send.
The source used Claude Cowork, which can take actions in a browser or app. These are general chat tools, so results may differ, and a normal chat may only give you a plan.
Opens in a new tab. We don't see what you send.
These links are only a shortcut. We're not affiliated with OpenAI, Google or xAI, and your results may not match the source.
Optional stronger version
Our rewrite with extra checks. The poster didn't test it.
Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to. Goal: Tidy up a messy desktop or folder without any risk of losing files. Fill in before running: - The folder to tidy, and nothing outside it: [FOLDER] - The folder structure I want: [STRUCTURE] - Any folders that must never be touched (photos, documents): [PROTECTED] Back up first. Point the agent at one folder, not your whole drive, and don't let it delete anything. If files vanish, check iCloud's Recover Files (iCloud.com, Data Recovery) or your cloud's version history straight away. Rules: - Before anything else, confirm I have a current backup, and stop if I don't. - Only move files; never delete, overwrite or rename folders. - Show me the full plan (from, to) and wait for my OK before moving anything. - Keep a log of every move so it can be undone. - Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify. Output: A move plan for approval, then a log of what moved where. You'll know it worked when: The folder is tidy and every file is still there. Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.
Source
Related cases
- Rename a pile of train tickets by date and destination with Claude CoworkRecreated promptEvidence: Described by poster
Claude Cowork read a pile of train tickets and renamed each file by its correct date and destination.
Claude Cowork · Personal · Source date:
- Turn an inbox into a daily to-do list with Claude Cowork (abandoned)Improved promptEvidence: Described by posterFailure
Claude Cowork summarized the poster's email into a to-do list, but the list grew long and unmanageable, so the poster stopped reading it and turned it off as a waste of tokens.
Claude Cowork · Personal · Source date:
- Organize a messy SEO work folder and rename screenshots with Claude CoworkRecreated promptEvidence: Shown on videoBeginner-friendly
Claude Cowork asked how the poster wanted 27 unstructured files organized, created analytics-data, blog-posts and screenshots folders, looked at each screenshot and renamed it by content (e.g. feature-text-to-sql-converter.jpg); the poster says it took about 30 seconds.
Poster says:27 files sorted in about 30 seconds
Claude Cowork · Ops · Source date: