Outlook (desktop & web) will no longer delete items from Deleted Folder

You need to check the status of the RecoverableItems subtree. When you permanently delete items, they actually end up in a hidden folder within the RecoverableItems subtree, where they are kept for the duration of the SingleItemRecovery period, or for the duration of any hold(s) applied to the mailbox. Depending on your situation, you have to follow the instructions in one of the two sections in this article: https://learn.microsoft.com/en-us/exchange/security-and-compliance/recoverable-items-folder/clean-up-deleted-items

Just to save you some headache, you might try doing the deletion via the webmail/OWA first. If you observe the same behavior therein, you (or an admin within your organization) will have to follow the steps in the article above.

Hi @Stephanie Emons

If you cannot delete it via https://outlook.office.com/, this indicates a server issue, or something block you permanently delete emails. Please do not try to delete the Deleted Items folder, it will not help in your case

First, please ask your IT to check if they have any hold or retention policy set up for your mailbox by using PowerShell.

Connect to Exchange Online PowerShell | Microsoft Learn and sign in with the admin account.

Connect-ExchangeOnline

Get-Mailbox ******@domain.com | fl *Hold*

If any of these are True or populated, permanent deletion is blocked:

RetentionHoldEnabled | LitigationHoldEnabled | InPlaceHolds | DelayHoldApplied | ComplianceTagHoldApplied

For example, below is one of my mailboxes and there is no hold that prevents permanently delete.

In your Classic Outlook, try right-click Deleted Items folder, choose Clear Offline Items.

Please verify and get back to me when you hear back from your IT admin.

I look forward for your reply.

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Based on the available information, the behavior described (items in Deleted Items reappearing after delete/move, folder effectively frozen) is not directly documented in the provided context, so only general, supported behaviors can be outlined.

In Outlook (desktop and web):

1. When a message is deleted from any folder, it is moved to the Deleted Items folder.
2. From Deleted Items, messages can normally be:
   • Permanently deleted (for example, by emptying the folder), or
   • Recovered from the Recoverable Items folder if the service and retention policy allow it.
3. When items are recovered from the Recoverable Items folder, they are placed back into Deleted Items, after which they can be moved to another folder.
4. In Outlook on the web, Deleted Items can be emptied manually, or automatically on sign-out if that option is enabled or if an admin policy empties the folder after a set number of days.

Given the context:

• Items restored from the Recoverable Items folder always go into Deleted Items first; they must then be moved elsewhere if they should not remain there.
• Deleted Items can be emptied manually (for example, by right‑clicking the Deleted Items folder and choosing Empty folder in Outlook on the web or Outlook Web App), which permanently deletes the items.
• Admin policies can automatically and permanently delete items from Deleted Items after they have been there for a configured number of days.

If Deleted Items appears “frozen” and items reappear after deletion, this is not covered by the documented normal behavior in the provided context. It would be necessary to work with the organization’s IT or Microsoft support to investigate account‑specific or service‑side issues beyond these documented mechanisms.

References:

• Recover and restore deleted items in Outlook
• Working with message folders in Outlook on the web
• Mail in Outlook Web App