Outlook keeps moving my sent emails to trash and there are no rules set up

Question

In Outlook Mail, my sent messages are automatically moved to trash folder. Even when I try to move them from trash to a folder, they go back to the trash folder. How do I stop this?

Answer 1

@Jonna Brigham
We seem to be missing each other with Questions and Replies, so I am adding a new Answer for a fresh start.

Please make your replies to this Answer by clicking in the "Add a comment" box just below this question.

Of my original questions I have your answers to #1

1 -- Is there a delay between when you move an email out of Deleted Items into a different folder before it jumps back into Deleted?

There is a delay and not all messages are moved.

I am still looking for your replies to my questions #2 thru #4

2 -- Are you in a MS 365/Exchange IT Managed environment? i.e. Is this a corporate/work email system? Or just your own personal email?

3 -- What is your email domain (the part after the "@" in your email address)? Do NOT reply with your full email address.

4 -- From Outlook please do File -> Office Account -> [About Outlook]. It should show a dialog like this.

Please provide the value you see in the top line. (You can right-click on that line and do Copy. So you can paste it into your reply).

Answer 2

Hi Jonna Brigham

From your follow-up, I understand you’ve already signed in to Outlook.com and confirmed there are no rules there.

From what you described, I understand that your sent messages are automatically moved to trash folder, you've already checked Outlook.com on the web and confirmed there are no rules there.

Have you already tried the steps in the Q&A Assist reply yet? If yes, what happened?

Also, could you try one test from Outlook.com in the browser:

• send yourself a short email from Outlook.com
• then check whether that copy stays in Sent Items on the web

If the problem happens only in Classic Outlook, please try these:

1, Start Outlook in safe mode

• Close Classic Outlook app completely
• Press Windows + R, type outlook.exe /safe > press Enter
• Try sending a test email in Safe Mode
• If Outlook is stable in Safe Mode, disable add-ins (Go to File > Options > Add-ins > Manage: COM Add-ins > Go) and re-enable them one by one to find the culprit.

2, Try to Repair Office (Online Repair) and, if needed, create a new Outlook profile:

Please follow the official troubleshooting steps here: Outlook crashes or stops responding when used with Office 365 - Microsoft Support

Looking forward to your reply so I can guide you with the best next steps. Thank you for your understanding.

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Answer 3

This behavior is almost always caused by a server-side rule or filter that runs before Outlook on Windows sees the messages, even if no rules appear in Outlook itself.

Use this sequence to stop it:

1. Check for hidden rules/filters in webmail
   • Sign in to the mailbox using the provider’s web interface (for example, Outlook.com, your ISP’s webmail, or corporate OWA).
   • Open the mail settings and look for:
     • Inbox / Mail rules
     • Filters
     • Sweep rules
   • Look for any rule that:
     • Moves all messages (or all sent messages) to Trash/Deleted Items, or
     • Moves messages whose subject does not contain some word to Trash (similar to the AT&T example where everything not containing “happy” was moved to Trash).
   • Disable or delete any such rule or filter.
2. Check Outlook rules in the client
   • In classic Outlook for Windows: Home > Rules > Manage Rules & Alerts.
   • Review all rules for actions that move messages to Deleted Items/Trash or to unusual folders (like RSS Feeds, as in a similar case) and disable/delete them.
3. Check for malicious or unwanted rules (if account was ever compromised)
   • If there is any chance the account was hacked (for example, after clicking a phishing email):
     • In webmail, check Mail → Rules and Mail → Forwarding for unknown entries and remove them.
     • Sign out of all sessions from the account security page and then sign back in.
4. Test after cleanup
   • Send a new test email.
   • Confirm it stays in Sent Items and is not moved back to Trash.

If the problem persists after removing all webmail and Outlook rules/filters, contact the email provider’s support, as they may have a server-level filter or security policy moving messages to Trash before Outlook can manage them.

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References:

• Where are my email messages or calendar events in Mail and Calendar for Windows 10?
• All Outlook 2024 email going to Trash instead of Inbox - Microsoft Q&A
• Stopped receiving emails on my account. - Microsoft Q&A
• Hacker set up continuous draft ransomware email - Microsoft Q&A