In new Outlook, emails stay in the outbox even though they've been sent.

Thank you Peter. I owe you coffee! That worked for me. I had given up after trying all other suggested methods to clear a stuck email message I had for weeks in Outbox, but simply moving it to Deleted Items did the trick for me. Usually, what happened was after deleting it using all other methods, the message will reappear in Outbox after closing and reopening Outlook. However, with your suggestion, it has not returned after closing/reopening Outlook.

For all it's worth, all other messages I had been sending for the past few weeks have been sent normally. It was only that one message that became stuck in Outbox, so I just moved that one message to Deleted Items and saw it was gone from Outbox. Then, I closed Outlook and reopened and it has not returned to Outbox. I will keep my fingers crossed.

This might seem odd but after reading all the forums and trying everything else I simply moved the messages from the Outbox into the Deleted folder and this worked perfectly. Then I deleted from the deleted folder and now the Outbox is empty.

I think there is a definite bug when using Drafts functionality whereby a Draft which is subsequently edited and sent then appears in the Outbox as Queued and never gets sent.

The broken workflow is :

Create email

Save as Draft

Move to Inbox to edit later

Perform edits

Send email

Email gets sent (visible in Sent folder)

Identical Email also stuck in Outbox and cannot be cleared except using the method above.

Ive spent hours working this out and fixing it and the solution was so simple.

Just to post an update-

We opened a ticket with our Microsoft vendor and they said that Microsoft is aware of this issue on the new Outlook client. We were told that we needed to wait for Microsoft to provide a fix or to switch back to the classic Outlook client.

If you can't switch to the classic client, you can also use the web version of Outlook, as this is not an issue there.

We have the same issue. I'll add a few more observations: Closing Outlook and Re-Opening Outlook resolves the issue until I send more e-mails. 2) Eventually they will be purged from the Outbox but that comes hours later. The e-mail has definitely been sent, since I get replies to it. They just sit in the Outbox marked as 'Queued'. Annoying. I can resolve it by closing Outlook and ReOpening. And that probably is the recommended resolution for Microsoft. But it's unacceptable for us.

Frustrated..

Does sending also "stick" for you? Late or no delivery of emails?

Smartest thing for me to do right now is use Google since it actually works.