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Internal/External Email

Last Modified: 2012-08-13
I have 1 local domain (domain.lan) (windows 2003)
I have 2 external hosted domains (domain.com, domain.net)
1 router (where my domain sits)
1 router which relays traffic to the net
Exchange 2003
GFI Mail Essentials for spam which downloads the email from my pop accounts and filters the spam (Installed on the exchange server)

Mail Essentials downloads the email and I have it being sent to an approriate account on my exchange server.

Problem: Outbound Email.
Sending from Outlook 2003
My Outlook profile is for my exchange server. (Resides on a gateway server)
When sending email, they just sit in the outbound queue until timing out.
Message tracking shows it submitted for remote delivery

I figure it may have something to do with my dns settings.  For this scenario, what should I have for dns entries to get my mail out?

Watch Question

Hypercat (Deb)President

Please give further details - what is the purpose of the two routers?  Since they are on the same subnet, it doesn't make sense to me.  Which router is being used as the default gateway?  Please post the IP settings for your Exchange server and the DNS configuration of your network.  What do you mean "GFI Mail Essentials...downloads the email from my pop accounts"?  MailEssentials doesn't download email from anywhere, it simply intercepts email coming in through your SMTP gateway and filters it.  Are you using POP accounts that reside on an external server?


Yes, I am using pop accounts from external servers.  GFI Mail Essentials does download emails from pop accounts.  If you are using external pop and need the mail to be filtered you need to use the Mail Essentials POP2Exchange.

2 routers because I have several computers within its own domain and some computers as standalone workstations where I still need access to them..  The default gateway is the router.
Exchange IP is  Dns is setup with the .lan namespace looking at the default gateway.

Hypercat (Deb)President

I forgot about the POP2Exchange - I've never used it ;-(  Still don't understand the need for a second router.  If all the workstations are in the same subnet, regardless of their domain membership, you would have access to them from any other computer that is on that same subnet.  Routing has to do with IP subnet not with domain membership.  I would just put everything on the same subnet and eliminate the second router.

Anyway, regardless of that, it sounds like the mail is getting from the workstation to your Exchange server, but is not leaving the server.   Sounds like it is maybe a firewall or DNS issue.  Can you browse the Internet from this server?  Is there possibly something on the router that is blocking outgoing SMTP traffic (port 25)? If you don't already have it on, you could try turning on SMTP logging to see if anything is even getting out beyond the router.  This setting is in the properties of the Default SMTP virtual server, on the General tab.  I recommend choosing the NCSA format instead of the default - it's easier to read.


Yes, I can browse the net from any workstation.  Smtp logging shows queued for remote delivery.  If I setup outlook to use my hosted domain mailserver or my isp mail server, there is no problem sending email (or receiving).  But I need the email to go back out through Mail Essentials to attach disclaimers and to be able to have Mail Essentials learn by outbound email for its bayesian analysis.

In DNS, should I have my dns pointing to my isp or to my gateway? (In network settings I have dns servers setup for both my gateway and my isp server).

As you can tell, I am a noob at DNS and Im trying to setup a forwarder, but Im not sure where the forwarder should be pointing (ISP dnsserver or my hosted domain dns server).
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