AD - I posted your request on another board and so far have received this reply from duittuit. If I receive any more, I'll bring them over - or you might watch that board for a couple days also.
I use Outlook 2002, but these are things I would do to troubleshoot the problem.
Close Outlook and reboot the system.
If that doesn't fix it, any of the following may.
Send a test message to veriry the account is working properly. They can look in Tools/e-mail accounts/view or change e-mail accounts/change. The send test message button is there. Just do not change anything!!
Go to Microsoft Update Page, link from the Windows Update Page and be sure that all fixes and security updaes are installed. When you change to MS update, it will update all of your MS software that needs it, so if you have illegal copies of anything you may have a problem doing this.
Be sure that the file is not larger than your e-mail provider will let you send. Sometimes an issue.
Zip the attachment. Sometimes makes a huge difference.
I was having copy and paste issues with Word the other day, hanging and not pasting, kind of the same thing in reverse, went to the MS update and something fixed it. LOL
(http://www.atomicbobs.com/index.php?mode=read&id=97139