Why does outlook have multiple old emails in my outbox when I open the program? Sometimes I need to restart my PC up to 4 times for them to clear

Question

Occasionally, my outlook will open with emails in my outbox. When I open the outbox, some of these emails are months if not years old and I know have been sent and replied to from the other end.

To fix this issue, I sometime have to restart the PC 3-4 times until its cleared and I can start using Outlook again. Has anyone else had this issue?

Answer 1

Hi Jayden, I haven't had the issue since but I will try the web app when it happens next and keep you updated.

Answer 2

Hi @Jake Fenech

May I ask if you are using Exchange, POP or IMAP account?

First, you can try Clear Offline Items by right click Outbox > Properties > Choose Clear Offline Items.

If the issue persists, for Exchange and IMAP account, try rebuilding your .ost file.

Press Windows + R > Type %LOCALAPPDATA%\Microsoft\Outlook\ > Look for your email address and delete if, then restart Outlook.

Some methods you can also try :

• Repair an Office application - Microsoft Support (Choose Repair Online)
• Create an Outlook profile - Microsoft Support(This doesn't affect your data)

Please try and let me know how it goes.

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Answer 3

This behavior typically indicates a send/receive or synchronization problem in Outlook rather than the messages actually being unsent.

Based on the documented symptoms, Outlook can show messages as stuck in the Outbox when:

• There are general Outlook sync or profile issues.
• The default folders or delivery location are damaged or misconfigured.
• Outlook is intermittently offline or cannot reach the server reliably.

To reduce or eliminate the issue, use the following checks and fixes:

1. Verify Outlook is online
   • In Outlook, go to Send/Receive and check whether Work Offline is enabled.
   • If it is highlighted, click it to return Outlook to online mode and then use Send/Receive → Send All.
2. Clear any genuinely stuck messages
   • In Outlook, select Send/Receive → Work Offline.
   • Open the Outbox.
   • Delete any messages that truly should not be there, or drag them to Drafts, open them, and re‑send.
   • Turn Work Offline off again to resume normal operation.
3. Repair default folders and delivery location Problems with the default folders or delivery location can cause symptoms such as messages appearing stuck in the Outbox and other odd behavior (for example, reminders failing, tasks not appearing, or search re‑indexing repeatedly). Use the /resetfolders switch to restore default folders:
   1. Exit Outlook.
   2. Open the Run dialog (Windows logo key + R).
   3. Enter:

            Outlook.exe /resetfolders
      

   4. Select OK and then start Outlook again and test.
   If folder names or structure look incorrect, also run:

      Outlook.exe /resetfoldernames
   

4. Watch for other profile issues The same class of issues that causes messages to appear stuck in the Outbox can also cause:
   • Reminders not appearing.
   • To‑Do bar showing no tasks.
   • Errors when trying to close a mailbox.
   • Desktop Search constantly re‑indexing Outlook.
   If several of these symptoms occur together, consider creating a new Outlook profile and re‑adding the account so Outlook has a clean configuration.

If the problem persists after these steps, collect details (frequency, whether it happens only after sleep/hibernation, network type, and any error messages) and provide them to support or in the Outlook community forums for deeper analysis.

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References:

• Outlook issues, including reminders that fail to appear, messages stuck in the Outbox, and Desktop Search indexing problems
• Outlook email stuck
• Email messages are stuck in Outbox in Outlook 2016 for Mac
• Outlook sync issues cause emails to be stuck in the Outbox and undeliverable mail items