Email Sync Problems

How to Fix Outlook Messages Repeatedly Reappearing in Trash

Tauseeq Magsi Oct 23, 2026 868 views

Question details

A message with a large attachment is stuck in Drafts and keeps duplicating into the Trash folder, quickly filling up the mailbox.

Fix Outlook Messages Repeatedly Reappearing in the Trash Folder

Product: Microsoft Outlook
Device & OS: not provided
Scenario: Attempting to delete an email with a large attachment that failed to send or got stuck in the Drafts folder.
Observed behavior: The deleted message reappears in the Trash folder repeatedly, generating hundreds of duplicate copies and consuming mailbox storage limits.

Before you start

Verify your internet connection is stable and try to log in to your email provider's webmail interface to see if the duplicates exist on the server.

Solution 1Recommended

Manually Empty the Drafts and Trash Folders

Repeatedly clearing out the local folders can sometimes force the server to acknowledge the deletions and break the duplication loop.

Delete the stuck message from Drafts

Open Microsoft Outlook, navigate to your 'Drafts' folder, select the stuck email with the large attachment, and press the Delete key.

Empty the Deleted Items or Trash folder

Quickly switch to your 'Deleted Items' or 'Trash' folder. Right-click the folder in the sidebar and select 'Empty Folder' to permanently purge the messages.

Restart Outlook

Close Microsoft Outlook completely and reopen it. Check the Trash folder after a few minutes to confirm that the duplication has stopped.

Manually Empty the Drafts and Trash Folders

Repeat the Process: You may need to repeat this deletion cycle two or three times before the local application and the server successfully synchronize the change.

Solution 2

Repair Your Outlook Data File with ScanPST

If the issue is caused by local file corruption preventing proper sync, repairing the PST or OST file will resolve the duplication loop.

Solution 3

Delete the Stuck Email via Webmail

Bypassing the local Outlook application and deleting the email directly from the server can fix persistent synchronization problems.

Free Microsoft Office alternative

Prevent Large Attachment Issues with WPS Office

Large attachments are a common cause of stuck emails in Outlook. WPS Office provides a free, highly compatible, and lightweight suite that lets you share large documents via cloud links rather than attaching them to emails, avoiding mailbox limits and synchronization failures.

1. Open your large document: Launch WPS Office and open the large file you intend to send via email.
2. Click the Share button: Navigate to the top-right corner of the interface and click the 'Share' button.
3. Create a sharing link: Select 'Create Link'. You can now copy and paste this link into your email body, avoiding the risk of the message getting stuck due to large file sizes.

Seamlessly compatible with Microsoft Word, Excel, and PowerPoint file formats.Easily generate cloud links to share heavy files instead of using bulky email attachments.Built-in file compression features to significantly reduce document sizes.Free and lightweight alternative to heavy desktop productivity suites.

microsoft office alternative - wps office

Frequently Asked Questions

Why do emails with large attachments get stuck in Drafts or Outbox?

Most email servers enforce strict attachment size limits (typically around 20MB to 25MB). If an email exceeds this threshold, the server rejects it. The local client then repeatedly attempts to sync or save it, which can trigger an endless duplication loop in the Drafts or Trash folders.

Will running ScanPST delete my existing emails or contacts?

No, the Inbox Repair Tool (ScanPST) is built to safely scan and repair structural damage within your PST or OST data files without deleting your personal data. However, as a precaution, you should back up your data file before beginning the repair.

What if messages keep duplicating even after repairing the local data file?

If repairing the data file with ScanPST does not resolve the issue, you are likely experiencing a server-side synchronization error. You should log out of your desktop client, log in to your email provider's web portal in a browser, and manually delete the stuck emails directly from the server.

Where exactly is the ScanPST tool located on my computer?

The location depends on the version of Office installed. For Office 2016, Office 2019, and Microsoft 365, it is commonly found in C:\Program Files\Microsoft Office\root\Office16\ or C:\Program Files (x86)\Microsoft Office\root\Office16\. Older versions may store it in the Office15 or Office14 folders.

Outlook & Email Problems