A client just called me, and they had three messages stuck in their Outbox in Outlook 2010 on a Windows 7 machine (though these instructions apply to other versions of Outlook and Windows as well). The messages had unusually large attachments, and Outlook could never send them before timing out (or getting stuck, not sure exactly what was holding them up). When I checked the Send/Receive Progress screen, it showed that the messages were being sent and had no errors listed. Here’s what I did to solve the issue:
- Clicked on the Send/Receive tab, and then clicked “Work Offline”.
- Closed Outlook completely.
- Open up Task Manager (you can usually do this by pressing control + alt + delete and then choosing “Open Task Manager”). Click on the “Processes” tab and make sure that Outlook.exe is not present in the list. If it is, click on it and press delete to close it down completely.
- Reopen Outlook. It should have remained in offline mode (you can verify this on the status bar at the bottom of the window or by clicking on the Send/Receive tab and seeing if “Work Offline” is still highlighted.
- Go to the Outbox, and you should now be able to delete the messages (if you just want to get rid of them altogether). Otherwise, if you want to modify the messages instead of deleting them, you can drag them into the Drafts folder and then edit them before attempting to send them again.
- When you are finished deleting or modifying the messages, remember to go back to the Send/Receive tab and click “Work Offline” again to deselect it, allowing Outlook to go back online.
After following these steps, we were able to delete the first message that was getting stuck and modify the second so that it would send. We thought the third message would send once the second one did, but it didn’t. We had to repeat the steps listed above to move the third message into the Drafts folder. After putting Outlook back online, we went into the Drafts folder, opened the message, and then clicked “Send”. The third message was finally sent successfully.