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deleted emails keep returning to the delete folder

Leanne Wehmeier 5 Reputation points
2025-12-15T05:54:55.47+00:00

I have deleted folders and they are in my deleted folder. When I "Delete All" they return withing a few minutes. How can I delete them so they stay deleted. I have tried all types of troubleshooting but they keep returning.

I cannot delete them individually as the "Delete Folder" is greyed out.

Outlook | Windows | Classic Outlook for Windows | For home
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  1. Mitesh Patel 0 Reputation points
    2025-12-15T17:55:28.3633333+00:00

    I have been having the same issue as well. I have done all the provided troubleshooting steps and still cannot permanently deleted emails from the Deleted Items folder to clear space for an M365 group mailbox. There are no retention policies or holds in place either for the group.

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  2. April P 5,435 Reputation points Independent Advisor
    2025-12-15T07:14:29.7033333+00:00

    Hi Leanne,

    This is April, I'll be happy to assist you. Sorry to hear that you're having issue with your Deleted emails. Let me help you out.

    Based on the description of the issue you provided, Deleted emails keep reappearing in the Deleted Items folder even after using "Delete All," and the option to delete folder itself is unavailable.

    When the deleted emails reappear, do they show the same timestamp and sender details as before, or do they appear as new items being synced back from the server?

    Your deleted emails keep coming back because Outlook isn't syncing properly with the email server. This is commonly due to a sync issue, server-side retention settings or a corrupted Deleted Items folder. Resolving it requires clearing the folder on the server, reviewing retention policies and repairing the Outlook data file.

    Here are steps that you can try on how you can permanently delete emails:

    1. Clear Deleted Items on the Server
      • Sign in to your email account via webmail (e.g., Outlook.com, Gmail)
      • Delete the emails directly from the web interface to bypass any Outlook synchronization issues.
    2. Check Retention Policies
      • If you're using Exchange or Office 365, confirm with your administrator whether retention policies or litigation hod are active.
      • These settings can automatically restore deleted emails.
    3. Repair your Outlook Data File
      • Close Outlook.
      • Run the Inbox Repair Tool (SCANPST.exe) to fix an PST or OST file corruption.
      • Restart Outlook and try deleting the emails again.
    4. Purge Deleted Items (For IMAP Accounts)
      • In Outlook, go to Folder > Purge > Purge Marked Items.
      • This permanently removes items from the server.
    5. Recreate your Outlook Profile
      • If issues persist, your Outlook profile may be corrupted.
      • Create a new profile and reconnect your email account
    6. Temporarily Disable Add-ins
      • Faulty add-ins can prevent email deletion
      • Go to File > Options > Add-ins and disable them to see if deletion works.

    The Deleted Items folder cannot be removed, only emptied. If the "Delete Folder" option is greyed out, this is normal. Use "Empty Folder" or "Delete All" instead.

    I hope this helps. If you need further assistance you can reply to this message.

    Thank you,

    April P.

    Independent Advisor

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  3. AI answer

    2025-12-15T05:55:04.2+00:00

    If deleted emails are returning to your Deleted Items folder in Outlook, it could be due to the Ignore status of the email thread. When a message is ignored, any future messages in that thread are automatically moved to the Deleted Items folder. To resolve this issue, you can follow these steps:

    1. Go to the Deleted Items folder.
    2. Find and select the message that is currently set to be ignored.
    3. On the Home tab on the ribbon, look for the Ignore option in the Delete section.
    4. If the Ignore option is highlighted, click on it and select Stop Ignoring Conversation when prompted.

    This should prevent future messages in that thread from being automatically deleted.

    If the issue persists, it may also be worth checking if there are any rules set up in Outlook that could be causing this behavior.

    References:

    AI-generated content may be incorrect. Read our transparency notes for more information.

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