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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

share|improve this question
    
So what is the question? –  mailq Oct 30 '11 at 0:16
    
I am unable to get exchange to forward to postfix. –  tbapb Oct 30 '11 at 0:20
    
This is not a question, this is a statement. –  mailq Oct 30 '11 at 0:28
    
Touche. Do i need an additional smtp connector or can i achieve this with only one? If so, what is the correct connector config to achieve the desired results? Thanks –  tbapb Oct 30 '11 at 0:56

1 Answer 1

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.

share|improve this answer
    
Thanks, this is great stuff. I had missed one configuration step where a new Recipient policy is created. I am still however unable to see any indication of mail delivery in postfix logs (/var/log/maillog). What is the best way to verify that exchange is actually trying to deliver the message to Postfix and does not drop it? –  tbapb Oct 30 '11 at 7:01
    
Use the Message Tracking tool in ESM to track the message and look at the SMTP log on the Exchange server to follow the SMTP conversation. –  joeqwerty Oct 30 '11 at 14:59
    
These are the last few lines of the logs in Message Tracking for the message in question: SMTP:Message delivered locally to multiple recipients SMTP Store Driver: Message delivered locally to store to email_Addy@example.com However, there is no indication of message delivery to jira-its@jira.example.com –  tbapb Oct 30 '11 at 17:58
1  
So the email is getting hung up at the external spam filter, which it shouldn't using method 3 unless Exchange is configured to send email via a smarthost. Is that the case? –  joeqwerty Oct 30 '11 at 21:49
1  
OK, do me a favor. Get everything back to their original settings. Get rid of the Recipient Policy, the Contact, the SMTP connector, and the DNS zone for jira.example.com. Then send an email from your AD account to jira@jira.example.com. You should get an NDR stating "The destination server for this recipient could not be found in Domain Name Service". If you do then we'll know we're back at square one and can start again from the beginining. –  joeqwerty Oct 31 '11 at 3:06

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