Solved

Exchange 2003 relay

Posted on 2011-03-18
14
258 Views
Last Modified: 2012-05-11
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,
0
Comment
Question by:rajaroraus
  • 8
  • 6
14 Comments
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35167095
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
0
 

Author Comment

by:rajaroraus
ID: 35167125
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.
0
 

Author Comment

by:rajaroraus
ID: 35167142
And I'm getting delays from domain names like Yahoo.com so I don't think it's and RFC compliance issue.
0
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35167148
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?
0
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35167150
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
0
 

Author Comment

by:rajaroraus
ID: 35167170
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
0
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35167174
Does the Ironport send to a Smarthost or via DNS?
0
PRTG Network Monitor: Intuitive Network Monitoring

Network Monitoring is essential to ensure that computer systems and network devices are running. Use PRTG to monitor LANs, servers, websites, applications and devices, bandwidth, virtual environments, remote systems, IoT, and many more. PRTG is easy to set up & use.

 

Author Comment

by:rajaroraus
ID: 35167249
Via DNS
0
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35167263
Okay - good.  Do you want to send me a test message?
0
 

Author Comment

by:rajaroraus
ID: 35167748
Just sent you one.
0
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35167822
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.
0
 

Accepted Solution

by:
rajaroraus earned 0 total points
ID: 35167967
Ok. I've removed the esmtp fixup/inspect option.  
0
 

Author Comment

by:rajaroraus
ID: 35794266
The issue was an access list on the firewall and not what was suggested.
0
 

Author Closing Comment

by:rajaroraus
ID: 35821621
The issue was on an access list on the firewall.
0

Featured Post

Is Your Active Directory as Secure as You Think?

More than 75% of all records are compromised because of the loss or theft of a privileged credential. Experts have been exploring Active Directory infrastructure to identify key threats and establish best practices for keeping data safe. Attend this month’s webinar to learn more.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Not sure what the best email signature size is? Are you worried about email signature image size? Follow this best practice guide.
Marketers need statistics and metrics like everybody else needs oxygen. In this article we explain how to enable marketing campaign statistics for Microsoft Exchange mail.
In this video we show how to create a mailbox database in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Servers >> Data…
To show how to generate a certificate request in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.:  First we need to log into the Exchange Admin Center. Navigate to the Servers >> Certificates…

947 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question

Need Help in Real-Time?

Connect with top rated Experts

18 Experts available now in Live!

Get 1:1 Help Now