I have been deleting emails in new outlook, and they keep coming back from deleted folder. In other words they will not stay deleted. Does anyone know why or how I can fix this problem. TIA

I'm done with hotmail/outlook. This has been happening to me for a long time, I have over 2500 emails in my email I can't get rid of. I've emptied the deleted folder, I used to be able to keep my email really cleaned up and delete daily and now I can no longer even use this email system. Complete trash and i'm sick of it.

I had a somewhat similar issue, but it wasn't with all emails, just a particular email. I'll describe my observations about the problem, and the solution I had to do to correct the problem. I was using the free outlook version that you get from upgrading the Mail app.

The email that I deleted seem to always be the first email in the inbox regardless if other messages are delivered later. If I select that email, I always saw two email selected. The deleted email would not show up in the Deleted Folder, and I noticed that other email folders I have created, would contain the deleted mail or would contain a an email that suspiciously looks like the same bogus email with some slightly different content and they would always be the first email in that folder. There seems to be like 6 or more forms of this same bogus email. They all displayed the "Ad" indicator and would only display the Delete button when you hovered your mouse over that message (i.e. this behavior was different from other emails where behaving on that version of outlook). If you clicked on the "..." button you would not see the usually options. One of the options said something like "run without ads". If you clicked on the email, it would take you to a web page (i.e. not open the email). In other words, there are a lot of bogus things about that email.

I deleted all the bogus message I found in every folder and then clicked on the synch. At that time things looked good, however, if I closed outlook and then reopened it, the bogus message would come back. I can access emails from my Android phone and from my MAC machine. Neither of those devices would have those bogus email. In other words, its not my email server that resending that bogus email. My conclusion was that my outlook app had been compromised.

The only way I could fix the problem was to delete the outlook app and re-install it. Rather then installing the Mail app, I installed Office 365 and now I'm using that version of outlook instead. I was planning to do that anyway!

Although my issue might not be exactly the same as the original post, it seems to me that it might be related. My observations suggests or hints at the possibility of a security vulnerability in at least one version of the outlook app.

There's one more thing worth mentioning! A few days ago I got a message when I opened the mail app indicating that I must update outlook before proceeding. I did do the update, since outlook wouldn't work without me doing that. Everything I saw made it appear as though it was an official Microsoft update. From the now perspective, I feel like I may have been dupped, and that may also be part of the hack. I'm pretty confident that the deleted email issue was occurring before I did the update, because I remember thinking that maybe the update would fix the deleted message issue I was observing. I do remember seeing the Microsoft App Store opening in my browser, but no interaction was required on my behalf. If this was an unofficial upgrade, the perpetrator is pretty sophisticated. I trust that the moderator, would pass this concern on to Microsoft Security Team for further evaluation.

I deleted all trash email yesterday, and they all re-apreared today, not a good email system, never had any issues with hotmail before

Forum helper

Also in addition to the Mod. answer, you can try

    this simple procedure. Hope it works for, you too

I had a similar issue, with a bunch of deleted

emails that, roll them back. What worked out. Was this trick ,.

       Posted this screenshot below. click the square [  ] Beside one of the 

    emails listed, then see above the [  ] **Recoverable items**  << click 

that square. Now all the **emails** on the list >> Get selected 

up next on the keyboard - Press the Shift + Delete keys : A Pop up with

          [***Do you want to permanently delete the selected items***] 

Appears >> click on [oK] All the checked emails get deleted...

Notice that : What's new here is when, the whole emails' group

get highlighted, when the Shift+Del shortcut is applied

This is the - ImageLink that appears : To click ok and finish the action

             Keep an eye. if they don't get back, in a few days. This deletion 

      method of using the : **Shift** + **Del**  work better than

the offered by outlook app : Try it on and post results

Hello SG_101824

Good day and thanks for reaching out.

The issue of deleted emails reappearing in the Outlook inbox after being removed from the Deleted Items folder can be annoying and time-consuming. This can happen due to several reasons. Some potential factors could be synchronization issues, server-side rules, corrupted Outlook profile and retention policies. Given the situation, we need more information on the following to narrow down the issue and better assist you.

1. Have you checked if your Outlook is syncing with another device or service that might be restoring those emails?
2. Have you looked into the recovery and retention policy settings for your Outlook account? Assign and view retention policies on email messages
3. Have you tried using Outlook, the Shift + Delete key combination to permanently delete selected emails without sending them to the Deleted Items folder?
4. Did you check if "Empty Deleted Items Folders When Exiting" setting is enabled in your Outlook?

5. If you end user, kindly ask your global admin to connect to Exchange online and run Get-Mailbox <ID> | fl *hold*. This command will show if there is any hold on your mailbox stopping the emails from been deleted.

Kindly let us know if the issue persists after implementing the above steps so we can proceed to the next step. Please understand that our initial response may not always resolve the issue immediately. However, with your help and more detailed information, we can work together to find a solution.

Thank you for your valuable time and cooperation.

Sincerely,

Bertrand