HI Experts I have a Windows 2008 Server with 2 IP's : 1.2.3.4 and 1.2.3.5 1.2.3.4 is the primary static IP in the TCP/IP properties and 1.2.3.5 is an additional IP i've added this server has installed IIS SMTP service, I have diffrent DNS recods that points to these IP: 1. xx.mydomain.com > to 1.2.3.4 2. yy.myotherdomain.com> 1.2.3.5 I also confiugured a PTR records and all communication works. now I want to have 2 SMTP virtual servers on the same physical server, so I configured each vitual server with he's own IP to port 25, and I added a valid hostname to the relay properties, configured the doamins I also followed : http://support.microsoft.com/kb/238131 , and it got me the right respones even though its was for windows 2003, since on windows 2008 SMTP relay is apart of the comatability pack for IIS6 it replied but when I telnet to 1.2.3.5 by IP or by yy.myotherdomain.com on port 25 and send email manualy and automaticaly, when I look at the header of the email it is allways replays from 1.2.3.4, the funny thing is that in the header I can see the yy.myotherdomain.com but it has the wrong IP in the header. I dont know what am I missing... any ideas will be welcomed thanks IdoG.

Hi IdoG, Thanks for posting here. This issue will mostly occur when multiple default gateways were set on server, could you verify it first ? If yes, you may need removing the default gateway entry that binding with the IP that appearing in the Internet header(1.2.3.4 in this case) form this server and see how is going . Meanwhile, multiple default gateways per server can have countless undesired effects. configuring a default gateway on a single NIC is always recommended. Thanks. Tiger Li TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.comPlease remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

Hi IdoG, If there is any update on this issue, please feel free to let us know. We are looking forward to your reply. Tiger Li TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.comPlease remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.