Exchange 2003 Outgoing SMTP delivery issues

Exchange 2003 Outgoing SMTP delivery issues

We have had an Exchange 2003 mail server for a few years and have had great results without many big configuration changes, until now. Recently we added a new Qwest T-1 and changed our firewall to a Watchgaurd. After the change we have had a number of problems delivering mail to certain hosts. These hosts require that your mail server send mail with certain mail header requirements.

I am trying to get input on what’s required on all levels for mail delivery.

For outgoing mail to pass header requirements what should be in place at your DNS provider Ex: A record, your ISP Ex: Reverse DNS, your firewall and internal Windows DNS server, and your Exchange server?

Currently our mail server is sending an EHLO that won’t resolve. The format is
Here is an example display of full headers received portion when I receive mail in my Yahoo account.


from (EHLO ( by with SMTP; Wed, 28 Jan 2009 19:14:08 -0800

What should this be? If the internal mail server is called “exch” can you use then rely in internal DNS to do the rest?

How should this also correlate with your ISP reverse DNS, should they matchup some how?

The solution was provided by Web: Twitter:
SPF or Sender Policy Framework will help your Exchange Server delivery mail smoothly.

Written by Roger Lund

VMware and Storage crazy man, vExpert, MN VMUG leader