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Exchange 2003 relay

We have an exchange 2003 server and are using it as a relay for a webserver which sends out confirmation emails once a person completes a registration. Lately, we've been getting a lot of messages saying that the email to this recepient has been delayed and eventually it comes back as undeliverable. I can't seem to find any reason why this is happening. The queue on the mail server shows no pending emails. I have resolved the mx records of the receiving domain and am able to connect to their mail server over port 25 getting a 220 response.

I am a little lost on this. Can someone assist?

Thanks,
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rajaroraus
Asked:
rajaroraus
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1 Solution
 
Alan HardistyCo-OwnerCommented:
Do you send to a Smarthost or via DNS?

Have you checked the configuration of your server to make sure it is RFC compliant?  My article should help you do this:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/A_2427-Problems-sending-mail-to-one-or-more-external-domains.html
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rajarorausAuthor Commented:
I do send it to a smarthost. It's a cisco ironport device that we have. This has just started happening recently. No changes have been made.
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rajarorausAuthor Commented:
And I'm getting delays from domain names like Yahoo.com so I don't think it's and RFC compliance issue.
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Alan HardistyCo-OwnerCommented:
Okay - so do your emails flow from the server to the Ironport device to the internet to other servers via DNS?

If so - you won't see anything queuing on the server as they will get pushed to the Ironport.

Is the firmware on the Ironport device up-to-date?
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Alan HardistyCo-OwnerCommented:
If you are not sure if you are RFC Compliant - drop me a test email to alan @ it-eye.co.uk - my Anti-Spam will tell me how you are configured and I can tell you how the world sees you and if they might have any problems with your configuration.

Alan
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rajarorausAuthor Commented:
I don't think so but I have checked the outbound queues on the ironport as well. There is nothing there.

Outgoing Mail Summary
Message Processing % Messages
 
 Spam Detected  
 0.0%  0  
 
 Virus Detected  
 0.0%  0  
 
 Stopped by Content Filter  
 0.0%  0  
 
 Clean Messages  
 100.0%  5,636  
Total Messages Processed:   5,636
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Alan HardistyCo-OwnerCommented:
Does the Ironport send to a Smarthost or via DNS?
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rajarorausAuthor Commented:
Via DNS
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Alan HardistyCo-OwnerCommented:
Okay - good.  Do you want to send me a test message?
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rajarorausAuthor Commented:
Just sent you one.
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Alan HardistyCo-OwnerCommented:
Got it - thanks.

Your problem is you have SMTP Fixup / ESMTP Inspect enabled somewhere, possibly on your Ironport device or you are behind a Cisco device that has this enabled.

When I telnet to your server I see the following:

220 ******************************************************

I should see something like:

220 mail.domain.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at Fri, 18 Mar 2011 18:07:35 +0000

Please remove the SMTP Fixup / ESMTP Inspect to prevent these sorts of problems.
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rajarorausAuthor Commented:
Ok. I've removed the esmtp fixup/inspect option.  
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rajarorausAuthor Commented:
The issue was an access list on the firewall and not what was suggested.
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rajarorausAuthor Commented:
The issue was on an access list on the firewall.
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