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I am transitioning from Exchange 2003 to 2007 and receiving a LegacyDN email address issue for external mail. Internal mail is working properly and all addresses are being resolved from the GAL. However, when a user sends mail externally, their email address appears as
<IMCEAEX-_O=_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=ADMINISTRATOR@organization.org>

Replying to that email address causes an NDR. If you send type the email address manually, user@organization.org. The email is sent and received without an issue.

I have been researching this all morning and can't seem to find anything that deals with the issue with external mail.

I have added the old X500 address in the ProxyAddress list for a test user, but am still experiencing an issue.
X500:/O=/OU=FIRST ADMINISTRATIVE GROUP/CN=RECIPIENTS/CN=@Organzation.org

When using OWA, the same issue occurs, so we can rule out anything dealing with the local mail client.

I have created a new mailbox and the external mail address works properly. This is only occurring with moved/upgraded mailboxes.

Does anyone have any ideas?

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I've never heard of this being a problem with external emails. How did you migrate the mailboxes? –  joeqwerty Feb 6 '11 at 21:01
    
@joeqwerty I migrated the mailboxes using the 2007 Exchange Management Console under Recipient Config -> Mailbox -> Move Mailbox. I went through the wizard and stated all of the mailboxes were moved successfully. They are all showing as being stored on the new 2007 server. –  Slambam Feb 6 '11 at 21:50

1 Answer 1

Check the primary smtp address for your users. Are they valid SMTP addresses? Looks like that for some reason they are the X500 addresses that match the LegacyExchangeDN, instead of the SMTP ones.

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