Emails stuck in outbox

Try these steps in classic Outlook on the laptop:

1. Check whether Outlook is offline.
   • Go to Send/Receive.
   • If Work Offline is turned on, click it to turn it off.
   • If the button was blue, Outlook was disconnected.
2. Open the Outbox and inspect the stuck message.
   • If it has a large attachment, remove it.
   • Large attachments are a common reason messages stay stuck.
   • For Outlook on Windows, messages with attachments larger than about 20MB can cause sending problems with some providers.
3. Put Outlook in offline mode so the message can be edited safely.
   • Select Send/Receive > Work Offline.
   • Open Outbox.
   • Either:
     • delete the message, or
     • drag it to Drafts, open it, remove the attachment, and save it.
4. If Outlook says it is trying to transmit the message, close Outlook.
   • If it does not close, press Ctrl+Alt+Delete and open Task Manager.
   • On the Processes tab, find outlook.exe and end it.
   • Reopen Outlook and repeat the Outbox steps.
5. Go back online and resend.
   • Select Send/Receive > Work Offline again to turn offline mode off.
   • Then choose Send/Receive all folders or Send All.
6. If messages only send when manually pressing Send/Receive, enable automatic sending.
   • Go to File > Options > Advanced.
   • Under Send and receive, turn on Send immediately when connected.
7. If the account password was recently changed when the account was recovered, update the saved password in Outlook.
   • A password mismatch can stop send/receive after an account recovery.
8. Make sure the laptop has internet access.
   • Open a browser and confirm websites load.
   • If there is no connection, Outlook cannot send.

If the Outbox shows a number but no visible message, Outlook may be repeatedly trying to send a stuck read receipt rather than a normal email.

References:

• Outlook email stuck
• I can't send or receive messages in Outlook
• Troubleshoot Outlook email setup
• Outlook keeps trying to send a nonexistent message while Outbox folder shows zero messages