Philip,
My experience with IronPort Support has been top notch,  I’d try giving them a 
shot at helping with your configuration.
Even though, of course, when it comes down to it they’re going to tell you 
they’re not Exchange experts, I’ve found them to be an incredible resource.

V/R,

Mathew L. Givan
[email protected]<mailto:[email protected]>

From: Phil Hershey [mailto:[email protected]]
Sent: Tuesday, December 14, 2010 9:18 AM
To: MS-Exchange Admin Issues
Subject: RE: Exchange 2003 & IronPort

I’ve tried using both the IP address and the .local FQDN on both the virtual 
SMTP server and the default SMTP connector, separately and in conjunction, to 
no avail.  Very frustrating.

From: RS [mailto:[email protected]]
Sent: Friday, December 10, 2010 12:54 PM
To: MS-Exchange Admin Issues
Subject: Re: Exchange 2003 & IronPort

When you write FQDN, do you mean the internal FQDN if it's different from the 
public one?  (e.g. ironport.domain.local -vs- 
mail.domain.com<http://mail.domain.com>)

Have you tried putting the ip address in the smart host settings?

On Fri, Dec 10, 2010 at 3:40 PM, Phil Hershey 
<[email protected]<mailto:[email protected]>> wrote:
Anyone out there in the ether have experience with configuring Exchange 2003 
with an IronPort from Cisco?  We had a test box in here for a month’s trial 
about 6 months ago.  Boxed it up, never sent it back to Cisco or the vender, 
and now we’ve purchased it after all.  The IronPort still has the configuration 
on that was working before, although I’ve installed feature keys for RSA DLP, 
Email Encryption, Anti-spam, Virus Outbreak and Sophos.

Problem is I obviously cannot recall how properly to set up the smart host 
settings on my Exchange connectors and virtual servers. I’ve tried entering the 
IronPort’s FQDN in the connector and virtual server settings, each separately 
as well as in both simultaneously. After each attempt I’ve restarted the 
Exchange Routing Engine and SMTP, but the outbound messages just start 
accumulating in the ‘queued for deferred delivery’ queue.

I’m obviously missing something simple and likely obvious, either on the 
Exchange or IronPort end, but I cannot figure it out.  Any obvious ‘gotcha’s’ 
that anyone would like to point out that I’m missing, either on the IronPort or 
Exchange server?

Philip


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