Delivery Failure Notice recieved email is sent via Outlook but the email goes through when sent via Yahoo?

I have a specific issue...each time i send something to my friend's email address using Outlook. I always get a 'Deliver Status Notification (Failure)' for the email sent. I always confirm with the recipient and he always confirms that he never recieves anythign from my Outlook.





Surprisingly, if I use my Yahoo account to send the email the email goes through...This has made me scratch my head countless times as I work in an IT firm and I could not solve this.





The error message comes as:


Reporting-MTA: dns;hesa01uker.he.local


Received-From-MTA: dns;c2bthomr11.btconnect.com


Arrival-Date: Thu, 15 Mar 2007 15:46:26 +0000





Final-Recipient: rfc822;jean_smith@btconnect.com


Action: failed


Status: 5.4.6


X-Display-Name: Jean Smith


-------------------





My guess was whenever I send him something using Outlook, the email is sent to another email address that is registered in BTconnect, but I have purged my address and have verified the properties of the email address. Any ideas?

Delivery Failure Notice recieved email is sent via Outlook but the email goes through when sent via Yahoo?
The problem could be related to firewall or antivirus settings. When you say that you send something using Yahoo if you mean webmail then the email isn't subject to your firewall and antivirus rules. If you send email using Outlook then it has to go through both before being delivered. To test this, turn off your firewall and antivirus softwares email scanning features, then send using Outlook. If it goes through you've found the problem. Of course, make sure to put your antivirus email scanning and firewall back up after the test. Good luck.
Reply:I would delete that email account in Outlook, reboot and then reset it up. I was getting the same type of errors when using outlook and that is what I did and it worked. I have no idea other then a POP was entered wrong.
Reply:You have to change your port to what yahoo recomends. I think it's 465 but check on that.
Reply:Is outlook using the Yahoo account or another email account? This sounds like a relay problem or some thing caught in an outgoing mail server.
Reply:A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients.


5.4.6 means "Rooting loop detected"





If your Outlook is configured to go through an Exchange Server, check out Microsofts support for detailed help.





http://support.microsoft.com/kb/324732