Two servers aren't routing messages properly

[ToyodaTim]

Ok, I think I know what is going on here but I need help on how to fix it.

I have two Exchange 2000 Servers configured. They are both hosting mailboxes for our SMTP email domain name mycompany.com. I have them in seperate routing groups, "Front End" and "Back End".

In both routing groups I have a Routing Group Connector configured to transfer messages back and forth. In the "Front End" routing group, I have a SMTP connector configured for our Internet mail. This connector is set to resolve messages by DNS for the address space "*" (it's my understanding that this will route messages to any domain, including our own mycompany.com, through this connector.)

As you may have already figured out, I can send mail from the server in the Back End routing group to the server in the Front End, but I can't send the other way. I am betting that the emails from the server in the Front End are being routed through the SMTP Connector to the Internet, which is pointing the message right back to the same server. Is there any way I can override this for our domain (mycompany.com) so that mail with this address space goes through the Routing Group connector? Maybe there's a way to exclude mail from mycompany.com on the SMTP connector?

Any help will be appreciated.

-Tim Nichols

 

[PScottC]

Is there a firewall between the 2 servers? Are there connections in both routing groups pointing to the other? If you have a firewall, is AD replicating and do both systems have connectivity to a global catalog?

PSC

 

[ToyodaTim]

There is no firewall present between these two servers or routing groups. These servers are both located in the same site physically (they are sitting side by side and are on the same subnet connected via a switch). I had to configure routing groups because when they were in the same routing group they weren't transferring email between them.

I was thinking that maybe the problem was in the configuration of either the SMTP connector for internet mail (using DNS to resolve address space "*&quot or in the configuration of our DNS server. I created an MX record in our internal DNS for both servers. That didn't seem to work. Now the messages are getting stuck in the Internal Routing Group queue on the old server (in the Front End routing group).

And yes, there is a routing group connector on both ends pointing at each other.

Any more ideas?

-Tim

 

[PScottC]

Have you added your company's address space to the recipient policy for your domain?

PSC

 

[ToyodaTim]

I checked and the company's address space is in the recipient policy.

I did a little more fooling around with this and here's some more information:

We have a web filter program that filters for junk mail listening on port 25, and the Virtual SMTP server for our old server is configured for port 26. I put both servers into the same routing group and the only connector is an SMTP connector for Internet Mail which uses DNS to route to the address space (which is "*&quot. When I put them in the same routing group, email doesn't go between the two internal servers at all. I turned off the web filter program and set the Virtual SMTP server port back to 25 on both new and old servers. When I did this, I was able to send email from the account on the new server to the old server, but sending email from an account on the old server to an account on the new server doesn't work. I get a 5.3.5 error saying that the messages are bouncing between two servers.

What is going on here? Is the SMTP connector screwing things up? Or is it possible that I need to work on my DNS configuration some more. Right now, DNS has MX records for our address space pointing back to the old and new servers with the same preference value.

Anyone else have an idea?

-Tim

 

[PScottC]

Yeah... You don't need the SMTP connector unless you are trying to force mail to be routed in a particular fashion. I would remove the connector. If you have multiple routing groups, use a Routing Group connector.

PSC