Forwarding mail from Exchange 2003 to Postfix

exchangejirapostfix

This has been kicking my butt for some time now and i'm reaching out for help.
Here is the scenario:
There is 1 Exchange 2003 server which lives on mail.example.com. It has 1 SMTP Virtual server and 1 SMTP Connector. The connector is configured to forward all mail through an external spam filter.

What I am looking to do is setup a ticket system (JIRA), which will live in a virtual machine on the same LAN as Exchange and should receive only internal mail destined for jira@jira.example.com. So i will have a distribution list on exchange – it-support@example.com which will have a contact member jira@jira.example.com. From what i've read i need another SMTP connector configured on exchange in order to process outgoing mail destined for jira.example.com. Postfix will be the receiving mail server for jira.example.com.
So far, i am struggling to see any indication of mail being routed to Postfix, but there are no bounces. Please let me know what you think.
Here is my attempt at a diagram 🙂
http://nulledge.info/display/NTS/Example.com+mail+routing

Problem: I am unable to get exchange to forward to postfix.

Question: What is the best way to verify that exchange is actually trying to deliver the message to Postfix and does not drop it?

Question #2: In the descried scenario, would exchange be considered a "relay" for postfix?
Thanks so much in advance!

Exchange is configured to send email via a smarthost

Best Answer

A couple of things:

  1. Exchange Server 2003 isn't automatically authoritative for subdomains, which is what jira.example.com is.

  2. There are a few different ways to accomplish what you need, detailed here:

http://support.microsoft.com/kb/321721

A third method, which I think is easier would be:

  1. Create an internal DNS zone for jira.example.com.

  2. Create an A record for the Postfix server in the jira.example.com zone.

  3. Create an MX record in the jira.example.com zone that points to the Postfix A record.

This method leaves your Exchange server unencumbered regarding the Recipient Policy and SMTP connector. I think this is cleaner and simpler. The only caveat is if you have an external subdomain in the example.com DNS zone for jira (jira.example.com) then internal resolution of DNS RR's for jira.example.com are going to break.