Using New Outlook on Windows for personal email, calendar, and contact management
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.