I have setup a VPN which is working fine. I have routed some traffic through it. Now what I need to do is have my SMTP server sending all traffic through the VPN. However when I go to the SMTP servers properties, I cant select the VPNs IP. How do I do this? OS: Windows Server 2008 R2 SP1

I am still having this issue and any help with it would be much appreciated.

Hi, From the problem description, I understand that you would like to use the VPNs IP in SMTP Virtual Server. As we know, SMTP virtual servers provide the Exchange mechanisms for managing SMTP. Each SMTP virtual server represents an instance of the SMTP service running on the Exchange server. You use Exchange System Manager to configure SMTP virtual servers that control the behavior of SMTP. At the same time, from my side, you could verify the properties of the SMTP virtual server. On the Access tab, you will find the Connection Control. You could specify the IP address to access this resource. Just like the figure below: You could assign your VPN IP address to access the SMTP virtual server. I hope the information provided above is helpful to you. Regards, JamesPlease 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.

I think you misinterpreted what I was saying. I want the server to send the emails using the VPN IP rather than the servers IP. Here is where I wish to set it so all outbound mail will go through the VPN.

You would like to use the VPN IP address to send emails? It can't be done. As we know, the SMTP virtual server is based on the server. All the emails will be done via the SMTP virtual server (IP Unassigned or Local server IP addrees). In short, the email sending behaviour is controller by your SMTP virtual server. And the SMTP virtual server is on your server. It's by design. I don't know why you would like to use the VPN IP address to send emails. If you would like to do that, you could consider change your server IP address. If you would like secure your connection, you could set the Authentication and certificate on the Access Tab under the properties of the SMTP virtual server.James Xiong TechNet Community Support

The reason for it is the server gets DDoS'd so much that we have to completely sever the BGP when this happens. Since the server is in Australia and mainly serves Australia and NZ people this doesn't matter to the services we offer. However when it comes to sending emails to hotmail, gmail etc, they all go to servers overseas so people are unable to get them since there is no international traffic in and out of the server. We have setup a VPN to tunnel a few things like logging in for a service which verifys a licence key etc which is routed through the VPN using route add 2XX.XXX.XXX.XX mask 255.255.255.255 XXX.XXX.XXX.XXX However I don't want to have to add the remote servers for every email server that our members/clients use. Perhaps you know of another way to achieve this?

The only way you could control SMTP to be sent through this tunnel is to use a SMTP Smart Host on the remote side of the VPN which is allowed to connect to the Internet. This SmartHost will then forward the outbound Emails to Hotmail, Gmail, or any other remote Email domain. A Smart Host is in fact nothing else than a Email Server that acts as a STMP relay server and accepts messages from your own SMTP server. But this requires that such a system is in place and properly configured! Details on how to configure your SMTP Service to use a Smart Host: http://support.microsoft.com/kb/303734 Just a suggestion, but if your server gets DDoS so much, then you might want to address this problem to your ISP. He might be able to offer you a security solution that provides you an initial protection before the traffic even reach your end and resolves the problem with the BGP when you are under pressure. Such a solution could be that the ISP is routing the inbound traffic to one of his firewalls first, filtering the bad traffic and then route it to you. // Johann

Just a suggestion, but if your server gets DDoS so much, then you might want to address this problem to your ISP. He might be able to offer you a security solution that provides you an initial protection before the traffic even reach your end and resolves the problem with the BGP when you are under pressure. Such a solution could be that the ISP is routing the inbound traffic to one of his firewalls first, filtering the bad traffic and then route it to you. // Johann I wish that could be done. However we are an online gaming community and simply do not have the funds for that. They just want to much money for everything and being in Australia means that anything bandwidth/server related is at least twice the price than what they are in America.

We can point to the IP by setting the smarthost setting on the SMTP virtual server. You must user the IP, not hostname. IP must be in brackets. [xxx.xxx.xxx.xxx] http://support.microsoft.com/kb/308161 http://social.technet.microsoft.com/Forums/en/winservergen/thread/4ae9a4f1-dd9d-415f-9ff4-a151a8ee32d4 Also: http://support.microsoft.com/kb/308161 Ketan Thakkar | Microsoft Online Community Support