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Trouble receiving mail from one outside domain after Exchange 2003 upgrade

Expert Peter terSteeg helps an Exchange administrator troubleshoot why his company cannot receive mail from one particular domain after an Exchange 2003 migration.

We recently migrated our single Exchange 5.5 server (non-cluster) to a new Exchange 2003 server (active/passive cluster). Our operating system is Windows 2003, no Service Pack and Exchange is at Service Pack 1.

We receive mail from a lot of outside domains, but we are having trouble receiving mail from one outside domain. We did not have trouble before the upgrade to Exchange 2003.

At first, it would appear that the mail was just vaporizing into cyberspace, so I had one of the users send a message to me at my work address and my home address. The message was received immediately at my home address. Three days later, it arrived in my work inbox. I checked the headers and found that the message left the sender's box right away, and was delivered immediately to my inbox after our server reported it as received.

The problem seems to only occur when the sender from the outside domain initiates the e-mail. If they reply to one of our e-mails, I have been told there is no delay. We also have no problem sending to them.

I am inclined to think that the problem is not on our end. However, there were no problems prior to the upgrade. There also doesn't appear to be any way to track down where the bottleneck might be.

What should I look for here? Should our FQDN be mail.ourdomain.com instead of the server name? What should I suggest that the sender look for? The sender is using Novell GroupWise Internet Agent 6.5.2. Is there an issue with GroupWise and Exchange 2003?

Any suggestions are appreciated as we have a lot of dealings with this company and my users are getting antsy.

I noticed that based on your domain name, you are part of a large state government implementation. I would definitely look into the mail flow from the test account, including every hop to the final server in your implementation.

I also telneted to port 25 on your MX record listing -- I am not getting an Exchange front-end response, so you may want to look at the logical and physical mail flow within your organization. Maybe there are antivirus or spam boxes that sit in the DMZ to accept and forward mail to your front-end Exchange 2003 server.

Do you have comments on this Ask the Expert Q&A? Let us know.
Related information from SearchExchange.com:

  • 11 tips in 11 minutes: Migrating from Exchange 5.5 to Exchange Server 2003
  • Tutorial: A primer on DNS and MX records
  • Free Download: Nslookup
  • Resource Center: Migration advice

  • Dig Deeper on Legacy Exchange Server versions

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