Microsoft Outlook + Sending Mail Issues

I'm experiencing a weird issue here with regards to Microsoft Outlook and sending emails. Outlook takes a long time to complete the sending mail task but does complete with no errors. The message is moved and is visible under the Sent emails. HOWEVER the receipeint NEVER receives the email.

Now before everyone assumes it is a mail server issue, here is the weird part. I can open up Outlook Express and sent emails through that application fine. So I figured it must be a configuration error. So I Imported the Mail Settings from Outlook Express into Outlook. This task went flawlessly, but outlook still is not sending emails properly.

Is this a fixable issue or a flaw with Outlook itself? Do I need to re-install Outlook?

 

Have you tried turning off your antivirus program to see what happens? Maybe Outlook has some conflict with the antivirus that Outlook Express doesn't or OE mail isn't being filtered by your antivirus?

 

Try to CC a copy of the mail to yourself; if you get it it should rule out your SMTP as an issue.
VV