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We are moving to a new hosting provider and hit a brick wall in configuring SM 5.5 on Windows Server 2008. We have identical settings between our current server (with a different provider), but the new server will not allow outbound SMTP connections from email clients or our ColdFusion Server. Sending email from the webmail interface works just fine.

We've eliminated firewall issues (no hardware yet, Windows Firewall was temporarily turned off completely). The server host is not blocking any traffic. 

The only difference between our existing production mail server and the new one giving us trouble is that the old is Windows Server 2003 and the new one is Windows Server 2008.

Any ideas or suggestions would be appreciated! I'm almost positive it's a Windows Server 2008 issue (I can not telnet to the mail server either), but can't figure out what it could be!

If you moved the domains from one server to another, they still may be trying to use the IP address from the old server. Edit your domains and see what IP they are trying to use. Alter the setting if need be and see if that helps.

Though it sounds like you may not have done the move, yet. Are there any domains set up in the new server yet? SmarterMail will not listen on any ports without a domain set up.

I've setup one test domain (a real domain but not one that is actively used). It's got all the MX records setup properly, we have reverse DNS setup, etc.

Could it be a Windows Server 2008 issue? Should SMTP be installed and active? I know on 2003 SMTP is not an active service, but not positive of the 2008 setup.

Thank you for your help.

Try to send a local message (if you have configured with localhost) or telnet localhost 25. If this connect, the problem is in the firewall on network.

First thanks for the responses. I've narrowed the problem down a bit. 

I can tenet to the first IP on the server, but Smarter Mail is assigned to the second assigned IP. Not sure this is clear, so here's my setup. The server has two public IPs:

x.x.x.66

x.x.x.67

The mail server is assigned to x.x.x.67 and I can reach SmarterMail Web Mail just fine. I can telnet to x.x.x.66, but not x.x.x.67 or using the domain name.

So it's not a firewall issue and not SmarterMail, I don't think, but rather tying the proper IP to SmarterMail. The correct IP is set in IIS 7, and I can verify that the DNS for the mail server domain is correct. I just can't telnet to the server using it's domain name.

Still looking for the solution though! How do I tell  Win 2008 that Smartermail is listening on x.x.x.67, not the other IP?

I finally re-installed SM 5.5 and used the primary IP on the server instead of the secondary one, short of finding a solution. I did confirm that the test domain was set to receive mail on the correct IP, which seemed like the likely culprit.

 I'm not sure if it was something stupid I did in the setup or a Windows issue, but I never could get SM to receive incoming SMTP connections on that secondary IP. Very odd.

I'm having this exact problem now on 6.5. Yesterday, all emails went down, havn't received emails in a day. Eventually found that mail.domain.com was pointing to the secondary IP which isnt responding to telnet 25, but the primary IP is.

Anyone found a solution?

I am not sure if this helps (since the post is old), but if you are using Windows Server 2008 R2 (possibly Windows 2008 too), you will find that there is no "primary" IP anymore. They are all "primary" or preferred. Apparently this is due to IPV4 keeping up with IPV6 regulations.

This created a big problem for us as some of our remote servers for our control panel system required us to list valid IP's the master server could communicate on. Usually this was one IP- the primary one. However, now we must list every IP.