Outlook 2013 and Office 365 - Mail is stuck in outbox.

If you move a message to Drafts, then open the message and click on Send, does it then send?

Or, if you move the messages out of the outbox, does a new email send properly?

Thanks for your help Guys.

Alan, On this setup the drafts folder says 'Drafts (This computer only)' and you can't drag and drop the message to the drafts folder. You get a no-entry sign if you try.

In fact I created a new folder and tried to move it to that, which looked like it was going to allow it, but then I get an error 'Service provider does not support this action).

Davis, see above. Can't move can only delete.

You just told me that the emails "stuck in the outbox" are on the server not the user's local storage.
If they are unimportant, delete them.  If they are important, copy and paste their contents or see if they will open so you can do a Save As.  Either way, they need to be deleted in Outlook so you can test a new email send.

There are only test mails in the outbox at the moment. I can delete the mail messages in the outbox and then create and try to send a new mail (different receipient) and get the same problem.

Is the Outlook.com being hosted by Microsoft or by a third party?  I ask because there ought to be events logged on the server.
Do you have another user who works that you could use to verify the settings?
And the normal, next step, (Ugh) would be to delete the profile using the mail icon in the control panel and then recreating it.

Thanks again Davis. The Outlook.com is at Microsoft and I've already tried deleting the profile and recreating it.

I'm not being silly here, am I? There is no restriction on a free Outlook.com account working with Outlook on a laptop, this should work, right?

Yes, it should.
1)  Delete the profile again.
2)  Go to Programs and Features in the control panel and REPAIR Office. (Uninstalling and reinstalling almost never fixes anything!)
3)  Reboot (no matter what it may say!)
4)  Test internet connectivity, preferably with IE.
5)  Use this to create the account, again: https://support.office.com/en-us/article/Add-your-Outlook-com-account-in-Outlook-for-Windows-642c1902-bdd9-4dc3-abe7-76d60b148b23?CorrelationId=e0c9af73-f603-4599-8f88-aa8ca724c93e&ui=en-US&rs=en-US&ad=US

Did that work?

Davis, I can confirm I have followed these instructions exactly as stated and have the same problem.

I have also checked on a Windows 7 laptop with Outlook 2010 and that works ok.

If you login via OWA on the 365 portal, can you create and send a test email happily?

on-line is fine.

That's always good.  Have you tried adding the same Outlook account to a different computer to see if the problem follows to that computer too?

I've tried it on Windows 10 with Office 2010, that works fine.

I've just built a Dell laptop from scratch with Windows 10 Ent, then loaded Office 2013 Pro and set up the account and had the same problem.

So this is either a fault in win 10/office 13 combination or the account itself is stuffed.

As the account works in Windows 10/Office 2010 combination I am forced to conclude that this is a win 10/office 13 problem, but why I don't know.

Any further suggestions?

Just testing on my Windows 10 Pro VM on my Mac (using Outlook 2013).

Back in a moment.

Seems to be working happily for me.

Have you exhausted Windows / Office Updates?

So, since you're using a free Outlook.com account, have you tried creating another account to test?

I have exactly the same problem, just upgraded to Windows 10, and on my Microsoft Outlook 2010, any new mail gets stuck in the Outbox, and is not sent out when doing Send/Receive.

I tried two solutions that I've found on the web:
1) Re-setup the POP3 connection to your mail server.
- that did not work  
2) Fixing file integrity issues on the outlook .PST "data" file which contains your e-mail.
This seems to work for a lot of people. Essentially you run a command in a CMD (DOS-prompt) window. More can be read about it here:
http://answers.microsoft.com/en-us/office/forum/office_2013_release-outlook/outlook-send-error-after-windows-10-update/c4e5a73b-4191-4d8f-bf79-e4c50c36a8db?tm=1438285150624

No offered solution worked although every suggestion was good.

In the end I had to get on and couldn't spend any more time on it.

Thanks again guys for your help.