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Exchange 2003 users cannot reply to email sent from migrated accounts

Learn how to troubleshoot when Exchange 2003 users cannot reply to email sent from newly migrated accounts and discover how the ADModify.Net utility can help.

I am the Exchange Server administrator at my company. We have about 5,000 accounts with close to 30,000 email addresses. We recently acquired a company, and they also use Exchange Server 2003. What is the best way to migrate their data into our system?

Here is what we did and why it did not work so well:

To make the new employees show up in the Global Address List (GAL), we created them as contacts. We gave them an email that matches our domain which forwards to their own domain. All our current employees can exchange email with the new employees.

However, during migration these contacts must be deleted, and mailbox-enabled users must be created in order to use the same email addresses, etc. The problem is that Microsoft Outlook and Entourage cache the email addresses. If a person replies to or sends a new message to a new employee, it tries to deliver the message to the contact. Since the contact is no longer there, the message bounces.

I've recommended that we migrate the users after hours on a Friday evening so we have the weekend to have a new address book pushed down to the client. If we move them during the week, we'll receive too many calls to our call center. To get around the problem, we can delete the cached address book and set the client to On-Line mode. This is an ugly solution.

As an administrator, I'd like to find a solution that is totally transparent to my end users. Do you have any suggestions?

You need to maintain the contact distinguished name (DN) as an X.500 address on the new Exchange mailbox object. You changed this during your migration when you deleted the original contact and replaced it with an entirely new object. The message is stored with the X.500 address at the time it was processed. To correct this, add an X.500 address to the user object in Active Directory (AD) that matches their old LegacyDN.

Read more about this issue in the Microsoft articles "Enabling replies to old organization after Move Server Wizard" and "Cannot reply to messages that are sent from a user account that was moved to a different site."

You should also take a look at the ADModify.Net utility. It's very useful because it allows you to make bulk changes in Active Directory. Microsoft provides more information on ADModify.Net.

Do you have comments on this Ask the Expert Q&A? Let us know.

Related information from SearchExchange.com:

  • Tip: ADModify.Net tool makes bulk changes to AD user and object records
  • Tip: Access contacts in an LDAP or X.500 directory from OWA
  • Expert Advice: Will admin.exe directory modifications work after migration?
  • Reference Center: Exchange Server deployment and migration advice
  • Reference Center: Exchange Server migration tools
  • Dig Deeper on Exchange Server setup and troubleshooting

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