Outlook Email stays in Outbox until you manually send it

The Outlook 2013 application in Office 2013 also follows same procedure while sending mails. But sometimes you may observe some peculiar behavior while sending mails with this component, such that:

• You send a mail from shared mailbox and it remains in the Outbox folder

• When you manually open the Send/Receive operation window, email is send automatically

In some cases, you may first see errors when you open Send/Receive dialog:

In few moments that paused email is sent:

Thus the problem here is that until you open Send/Receive dialog manually, the email is not sent and remains in Outbox, indefinitely. Here is how you can get rid of this problem:

Outlook Email stays in Outbox

Registry Disclaimer: The further steps will involve registry manipulation. Making mistakes while manipulating registry could affect your system adversely. So be careful while editing registry entries and create a System Restore point first.

1. Press Windows Key + R combination, type put regedit in Run dialog box and hit Enter to open the Registry Editor.

2. Navigate here:

HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\Preferences

Substitute the placeholder x.0 with 15.0 for Outlook 2013, 14.0 for Outlook 2010, 12.0 for Outlook 2007, and 11.0 for Outlook 2003. 

3. In the right pane of above shown window, look for the registry DWORD (REG_DWORD) named DelegateSentItemsStyle, it must be having its Data set to 1. Double click on the same DWORD to modify and get this:

4. Finally, in the above shown box, set the Value data to 0 and click OK. Close the Registry Editor and reboot the machine to get this problem solved.