Outlook emails that take 2 attempts to delete

Question

Outlook emails that take 2 attempts to delete

Simon Neate-Stidson 0

Every day when I clear my Outlook inbox (in desktop Chrome browser) with emails I don't want, it takes 2 attempts to delete every email. When I click on DELETE it pops back into my inbox about 10 seconds later. Then I have to click DELETE again on every email, then it works on the 2nd attempt. It seems to only be when I open up emails in the morning, not later in the day. Not a huge problem but very annoying when it is every day, every email.

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2 answers

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Answer 1

Vikki-T 14,115 Microsoft External Staff Moderator

Hello Simon Neate-Stidson,

I understand how irritating this can be, especially when the same behavior affects every message at the beginning of each day.

Since you mentioned using Outlook in the desktop Chrome browser, it appears that you are using Outlook on the web, rather than the classic Outlook for Windows application shown in the current tag. Therefore, troubleshooting steps involving Outlook Safe Mode, add-ins, or Windows profiles would not apply here.

Does the Chrome tab remain open overnight? Before deleting any messages tomorrow morning, please close the existing Outlook tab completely, open a new tab, sign in again, and then try deleting one test email. Alternatively, press Ctrl + Shift + R to force the page to reload before testing. If the email deletes normally after doing this, the issue is more likely related to an older browser session rather than the mailbox itself.

Please also confirm whether you are using a personal Outlook.com/Hotmail account or a work or school Microsoft 365 account, as the appropriate support route differs between the two.

If the message still returns after approximately ten seconds even in a newly opened session, you can contact Outlook.com Support by selecting Help in Outlook on the web, entering the issue, and choosing Still need help? when offered. You can also review Microsoft’s official guidance here: Delete email in Outlook.com.

Please let me know whether closing the overnight tab or refreshing the page before the first deletion changes the behavior. Thank you so much for your understanding.

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.

Simon Neate-Stidson 0 Reputation points

2026-10-30T14:00:10.77+00:00

Thanks. It seems to only be in Chrome, so I've removed the entries as per suggested above. Seems to have worked this morning. THANKS!
Simon Neate-Stidson 0 Reputation points

2026-10-30T14:02:50.29+00:00

Thanks Vikki. I followed the AI instructions suggested below yesterday, seems it was only in Chrome, so I went do DATA& Permissions and removed entries associated with Microsoft. Seems to have worked, for now anyway. Will keep your suggestion in mind if the problem comes back. Thanks again.
Vikki-T 14,115 Reputation points Microsoft External Staff Moderator

2026-10-30T14:09:36.3733333+00:00

Hello Simon Neate-Stidson,

Thank you so much for the update, and I'm truly very happy to hear back from you.

If you ever have any other questions or run into anything in the future, please feel free to post your question on the Microsoft Q&A Forum anytime. I’ll always be here and ready to assist you.

Wishing you a great experience ahead!
Simon Neate-Stidson 0 Reputation points

2026-11-12T08:57:15.11+00:00

Sadly it's started again. Exactly as before: waits a few seconds after I delete each email, then it just pops back up. But just the first few emails (maybe 4 or 5), then it's fine. Baffling.
Vikki-T 14,115 Reputation points Microsoft External Staff Moderator

2026-11-12T13:14:41.64+00:00

Hello Simon Neate-Stidson,

Thank you for sharing this additional detail. Since the problem now occurs only with the first four or five emails and then stops, it appears more likely to be related to the initial Outlook web session or mailbox synchronization.

Before deleting the first email next time, please press Ctrl + Shift + R, wait about 30 seconds, and then test again. If the emails still return, please report the issue through Help in Outlook on the web and select Still need help? when available. Be sure to mention that only the first few deletions fail and that the messages return after several seconds, as this specific pattern may help Outlook Support investigate the synchronization behavior.

Official guidance is available here: Delete email in Outlook.com.

Answer 2

Delete a test message in another browser, then refresh and sign back in; whether it stays deleted will identify this as a Chrome-local problem or a mailbox synchronization problem.

1. Isolate the problem

Close Outlook on any phones, mail apps, and other browser tabs temporarily.
Open the mailbox in Microsoft Edge or a Chrome Incognito window.
Delete one unwanted test message.
Wait at least 15 seconds, refresh the page, then sign out and back in.

If the message remains deleted: the problem is local to the normal Chrome profile. Continue with the Chrome steps below.

If it returns: the first deletion is not being retained by the mailbox, or another connected client is restoring the earlier state. Skip to Mailbox-side checks.

Microsoft has previously documented this exact Outlook.com symptom—messages deleted from the Inbox returning to it—although that entry is an older investigation rather than confirmation of a current widespread incident.^1^

2. If it happens only in normal Chrome

In Chrome, temporarily disable ad blockers and privacy extensions for Outlook.
Reload Outlook and test one message again. Microsoft documents that AdBlock and uBlock can interfere with Outlook.com and recommends excluding Outlook.com or testing another browser.^1^
If it still happens, clear Outlook’s Chrome site data:
- Open Chrome Settings → Privacy and security → Third-party cookies → See all site data and permissions.
- Search for outlook, live, and microsoft.
- Remove the entries associated with Outlook, close all Chrome windows, reopen Chrome, and sign in again.
If that resolves it, re-enable extensions individually to identify the conflicting one.

This signs Outlook out in Chrome and may clear site preferences, but it does not delete mailbox content.

3. If it also happens in another browser

Check for something writing the old message state back to the mailbox:

In Outlook on the web, open Settings → Mail → Rules.
Temporarily disable rules that move, copy, redirect, or otherwise process Inbox messages.
Sign out of Outlook on phones and other computers, and temporarily disconnect non-Microsoft mail applications.
Repeat the delete-and-refresh test.

Comparable reappearing-message cases identify server-side rules and connected devices or applications as possible sources of restored message states.^2^

If this mailbox receives mail from a connected external account, such as Gmail, delete a test message directly in the originating account. Microsoft’s documented workaround for connected-account messages that reappear is to delete them at the source.^1^

4. Escalate if the deletion still reverts

In Outlook.com, select Help, describe that the first delete reverts after approximately ten seconds in multiple browsers, and choose Still need help? → Yes to contact Outlook.com support.^3^

Include:

Whether it occurs in Edge or Chrome Incognito.
Whether the message returns after refresh and after signing back in.
Whether all other mail clients were disconnected.
Whether the mailbox is an Outlook.com address or a connected third-party account.
The approximate time of a failed deletion.

References