I'm running an Exchange 2003 server which hosts several domains. I'm familiar with the Default Recipient Policy construction and have multiple users that have mulitple email addresses and have differing domain names, all working just fine. At least until I added the most recent domain. The goal was to add support for a new domain and have one user use that new domain as his primary address.
So here's what I did:
* I added the new email address email@example.com to the users AD user account.
* Remembering that I needed to add new-domain.com to the default recipient policy, I went and did that and set this Exchange server as responsible for delivery to this domain.
* I tried sending mail from this user to an external email account.
However, when I receive mail from firstname.lastname@example.org it shows as being from email@example.com. The firstname.lastname@example.org address is Set As Primary (and is bold in the list) and the magical "Automatically update e-mail addresses based on recipient policy" is not checked. If I change the primary address to email@example.com the from address changes to firstname.lastname@example.org. I can create another email address for this user of email@example.com and that works just fine.
If I create an address in my account in the format firstname.lastname@example.org, it comes through as email@example.com. If I select firstname.lastname@example.org as primary, that works fine.
Oh, if I try sending mail from email@example.com to firstname.lastname@example.org when everything is set how it looks like it should be set, the mail comes through the Exchange server as from email@example.com; it seems that the from header only changes when the mail actually leaves the system and that the problem is only with this new domain.
One final note. I also use ASSP as my spam filtration system. It works great and I suggest everyone use it. Anyway, the maillog of ASSP sees the outbound from as firstname.lastname@example.org, but the receiving server still sees it as email@example.com. I have tried pulling ASSP out of the mix and there is no change in behavior, from-header-wise. I have also sent mail through several different receiving servers using different OSes and different MTAs.
I've rated this question high due to its difficulty. I know what I'm doing (or at least I think I do!), and I'm stumped!