Are you setting smarthost on the VS or on the connector? You should be doing so 
on the connector, not the VS.

I honestly can't remember if you need a separate connector for the internal 
address space - I don't think so, as long as you have the smarthost set on the 
SMTP connector vs. the SMTP VS.

As to why outgoing mail queues up, if you are convinced it isn't "SMTP FIXUP" 
then I'd turn on detailed logging on the connector and examine the protocol 
logs.

Regards,

Michael B. Smith
Consultant and Exchange MVP
http://TheEssentialExchange.com

From: Phil Hershey [mailto:[email protected]]
Sent: Friday, January 21, 2011 10:42 AM
To: MS-Exchange Admin Issues
Subject: RE: Smart Host Setup, Exchange 2003

Hi, Michael.

That's not it, I don't think.  Email between the Exchange servers is over a 
pair of T3's, just another subnet.  Isn't the traffic between our two Exchange 
servers direct, the virtual SMTP servers and the SMTP connectors being solely 
for external messages?  That traffic never sees the firewall.  Do I need a 3rd 
connector with our own domain names in the name space with yet a 3rd SMTP 
virtual server?

Thanks for the quick response.  As usual.



From: Michael B. Smith [mailto:[email protected]]
Sent: Friday, January 21, 2011 7:14 AM
To: MS-Exchange Admin Issues
Subject: RE: Smart Host Setup, Exchange 2003

No SMTP fixup.

Regards,

Michael B. Smith
Consultant and Exchange MVP
http://TheEssentialExchange.com

From: Phil Hershey [mailto:[email protected]]
Sent: Friday, January 21, 2011 9:49 AM
To: MS-Exchange Admin Issues
Subject: Smart Host Setup, Exchange 2003

Good morning, all.

My problem is with setting up a Cisco IronPort appliance to work with our 
Exchange 2003 servers.  We had one in here last summer, and had it working 
correctly.  Well, the $$ finally shook loose to purchase a unit for each of our 
two offices.  We're going to use them solely for processing outbound email for 
HIPAA compliance and DLP.  Problem is that I cannot get the Exchange smart host 
settings correct.

Back when we had the demo unit, I saved off its working configuration, and this 
is what I've loaded into the new unit in this office.  (Back then we also had 
only a single Exchange 2003 server here in the home office.)  I then go to our 
default SMTP virtual server and to a TLS-enabled virtual server and set the 
smart host for both to the IP address of the IronPort appliance, 
[xxx.xxx.xxx.xxx].  As soon as I then restart the Exchange Routing Service and 
the SMTP service, messages stop being delivered and start accumulating in the 
queues.  Messages outbound begin to back up, and messages to our 2nd Exchange 
2003 server in our other office start to accumulate as well.

I've tried entering the address for the IronPort appliance in the smart host 
settings for the virtual SMTP servers alone, for the connectors alone AND for 
setting the smart host on both the virtual servers and the connectors at the 
same time.

I have used TELNET to connect from the Exchange server to the IronPort and to 
manually send messages, so I know the relay settings are correct on the 
IronPort to accept and forward messages from the Exchange servers.

Each Exchange server has 2 connectors - the default SMTP for the * address 
space (bridgehead is the default SMTP virtual server), and a TLS-enforced 
connector with the address spaces of companies with whom we have encryption 
requirements (bridgehead is the TLS-enabled virtual server with its own IP 
address).  Each connector is set to use internal DNS servers to route each 
address space on the connector.  Each has our Exchange server here in the main 
office as the bridgehead server right now, as all messages going out to the 
world will go through here and the IronPort I'm trying to get working here.  
Once everything is working properly, I'll be off to the other office to setup 
its IronPort and then its Exchange server  too will be a bridgehead that 
forwards out through that office's IronPort.

I'm sure I'm missing something that will seem obvious to me once I find out 
what that is.  I've been trying to research this for 2 days, and the longer I 
beat my head against it the dumber I feel.

Any ideas on this lovely Friday?

-Phil, Carpinteria, CA

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