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

Question

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

Stephanie Emons 0

My deleted folder recently stopped allowing me to permanently delete items. I cleared out the Recovery folder around 2/24 and the last emails that were listed in the Recovery folder were around 2/11/26. Since 2/24 (or when we noticed), I can no longer permanently delete items. Items marked as Deleted will repopulate in the Deleted folder at refresh. I cannot move items out of the Deleted folder (in an effort to rebirth the folder). The Deleted folder is essentially, frozen. We have synced the web and desktop versions and the numbers match and all seems to be synced. Our IT team hasn't seen this before. Any recommendations? I don't want to delete the entire Deleted folder, but part of my file maintenance is periodic review and removal of non-needed Deleted items. Thanks.

Jack-Bu 6,770 Reputation points Microsoft External Staff Moderator

2026-03-24T12:31:50.92+00:00

Hi Stephanie

It’s been a while since we last connected.

Glad to hear Jayden’s response helped clear things up! If you have any other questions or need further clarification, feel free to reach out anytime. And if you found this discussion helpful, please consider clicking “Accept the answer” to mark it as resolved. It helps others with similar questions and supports a stronger, more informed community.

3 answers

Your answer

Jack-Bu 6,770 Reputation points Microsoft External Staff Moderator

2026-03-24T12:31:50.92+00:00

Hi Stephanie

It’s been a while since we last connected.

Glad to hear Jayden’s response helped clear things up! If you have any other questions or need further clarification, feel free to reach out anytime. And if you found this discussion helpful, please consider clicking “Accept the answer” to mark it as resolved. It helps others with similar questions and supports a stronger, more informed community.

Answer 1

Jayden-P 21,315 Microsoft External Staff Moderator

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*

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

User's image

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

I look forward for your reply.

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Vasil Michev 126.5K Reputation points MVP Volunteer Moderator

2026-03-12T15:06:19.3166667+00:00

This answer is misleading/incorrect. The mailbox being on hold does not mean that the user cannot (hard) delete items or empty the Deletes items/Recover deleted items container. Holds do matter, but the culprit here is most likely the RecoverableItems quota.
Stephanie Emons 0 Reputation points

2026-03-12T17:23:46.2233333+00:00

Thank you! We do not have any holds on the my account. I did try removing the Offline items and believe that may have helped alleviate the problem. I am waiting for the online and desktop versions to sync.
Jayden-P 21,315 Reputation points Microsoft External Staff Moderator

2026-03-13T07:35:30.52+00:00

Hi @Stephanie Emons

If you have any news, please keep me updated. If the issue persists, you can check out Vasil's answer.

The behavior you are seeing matches with this document. It could be due to RecoverableItems quota hitting the limit like Vasil mentioned.
Jayden-P 21,315 Reputation points Microsoft External Staff Moderator

2026-03-13T08:41:39.35+00:00

Hi @Vasil Michev

Thanks for your additional and helpful insights, I appreciate it.

At first, I was relying on this table of actions, but then I tested myself, with litigation hold, I was still able to purge as user-level.

So, it means that the user can still empty the Recoverable Items, but Exchange will store a copy.

I will adjust the information above to avoid any misunderstanding.

Anyways, thank you for clarifying and providing helpful information.
Jayden-P 21,315 Reputation points Microsoft External Staff Moderator

2026-03-16T14:34:18.76+00:00

Hi @Stephanie Emons

Is there any update from you? Do you still meet this issue?
Stephanie Emons 0 Reputation points

2026-03-16T15:03:30.67+00:00

The clear offline items seemed to work. After I completed that step and restarted the program, I was able to successfully delete from the Deleted folder, and items are populating the recover folder again. I believe the problem has been solved. Thank you!
Jayden-P 21,315 Reputation points Microsoft External Staff Moderator

2026-03-16T15:09:43.9733333+00:00

Hi @Stephanie Emons

I am so glad to hear that.

If my answer helped you, please kindly mark it as accepted answer.

Warm thanks and if you need anything else, feel free to ask me.

Answer 2

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.

Answer 3

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):

When a message is deleted from any folder, it is moved to the Deleted Items folder.
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.
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.
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:

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

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