Do you have a situation where you can’t send e-mail after editing a “waiting to be sent” e-mail in your outbox? I helped someone with the same situation, read how I troubleshooted and found the solution.
This problem occurred in Outlook 2013 but could very well happen in earlier versions. This user disabled the option to “Send immediately when connected”
After composing and sending e-mail, it would be moved to the outbox. The actual sending of the e-mail would only happen when the user initiated a manual “Send and Receive”.
When editing an e-mail which was waiting to be sent (in the outbox) the icon would change from “waiting to sent” to a “draft”:
E-mail waiting to be sent in Outbox:
After editing the e-mail which was located in the outbox, the icon changed to draft:
As soon as you will press “Send” in the edited e-mail, the icon will change again to the little envelope and the e-mail would be sent after manually pressing “Send and Receive”. So far, this is all by design.
In this scenario, after pressing “Send” the e-mail would retain the draft icon and therefore would never leave the building. We found no way of sending an e-mail which was edited in the outbox.
How to troubleshoot
I tested it on a different machine and the behavior was different, an e-mail which was edited in the outbox would be waiting to be sent after hitting “send”.
To test if any plugins are responsible for this behavior we started outlook in safe mode:
When Outlook was running in safe mode, no plugins are loaded and the problem did not occur!
The quickest way to find the responsible plugin is by simply eliminating them, enable a few and restart outlook (not in safe mode) and see if the problem occurs.
After doing a few test I found the responsible plugin:
After disabling the iCloud plugin the problem did not occur.
This user did not use the Outlook functionality of iCloud so disabling was the solution. If the functionality is used, an update or follow-up with the vendor would be necessary.