There are a few reasons a message may get stuck in the Microsoft Outlook 365 Outbox. Here are the most common problems and solutions.
Reason 1 – Recent Password Change
Did you recently change your login password? Perhaps Outlook still is working off the old password. Try closing and restarting Outlook. You should be prompted to enter your password again. If that doesn’t work, try restarting your computer to reset everything.
Reason 2 – Message is Too Large
Check to make sure the message isn’t too large. Have a look at the Outbox. If the size for the message is over 5MB in size, it can sit there for a while trying to send. You can let the message sit there and see if it eventually goes or try to reduce the size of the message. If you have an attachment, try compressing the attachment using WinRAR, Winzip, or using the built in Windows method.
Clearing the Item from Outbox
If you want to just surrender and delete a message from the Outbox so that you may resend it, here’s the best way to do so.
- Exit out of Outlook or go to the “Send / Receive” tab and select “Work Offline“.
Select “Start“, then search for “Outbox” in the Start Search area.
- The item(s) in the Outbox should appear in the search. If you want to view and copy the contents of the email before deleting it from the Outbox, you can open it from here. You can also delete it by right-clicking it and selecting “Delete“. It will finally remove the item from your Outbox.
- Now go back under “Send /Receive” and select “Work Offline” again and resume your workday. The message should no longer be stuck in the Outbox in Outlook.
Note: These steps are based on MS Outlook 365 client for Windows 11, 10, 8, 7 and Vista.