This issue of a message being stuck in the outbox is a very common
occurrence with Windows Mail.
A successful fix has been developed by Steve Cochran:
Go to
http://www.oehelp.com/WMUtil/
Be sure to read the Program Operation notes! When you start to
download the file, be sure to choose Save rather than Run.
After wmutil.zip finishes downloading, choose Run, then Extract. Then it
will show the extraction folder with two files in it, WMUtil.exe and scxout.dll.
Run WMUtil.exe, wait until the buttons become active, then click on
Clear Outbox. It may take a while. Before you start, make sure
Windows Mail is not running.
Good luck.
Gary VanderMolen