I've got a hosted exchange solution through Apptix, which isn't the problem, I think, but it may be relevant.
I have my main account, [email protected], and to that, I have an alias, [email protected].
Whenever I send an email to [email protected], I examine the headers, and I see the "To:" field being correct, "To: [email protected]". All is well.
I recently set up another user, [email protected] to function as a multipurpose mailbox. I aliased "[email protected]" to the services account in the same method that I did "[email protected]", however nothing I have sent to "[email protected]" actually goes TO "[email protected]". All of the headers say "To: [email protected]". This makes it extremely difficult to filter based on headers alone.
Does anyone have any feedback on what settings I would need to look at in order to fix that?
An alias may not be what you want to do. What you should do is setup a separate email account and set that to forward to [email protected] without delivering to its own mailbox. This will keep all headers in tact.
I think it depends on how/where the alias is set up in the hosting provider. Since you are using hosted Exchange I am not sure what level of access you have to the actual Exchange server itself. (nor have I ever used a hosted exchange solution) Anyway strictly speaking, on the Exchange server if you set up the alias as an additional e-mail address on the user account itself, then the header in the received e-mail should reveal the ACTUAL e-mail address used in sending the e-mail to that user. ([email protected])
If, however, you do not have direct access to the Exchange server to add the e-mail address to the account yourself, the hosting provider (or whoever set up the alias) may have set it up on a system (e-mail gateway of some type) in front of the actual Exchange box as an alias there, which would redirect e-mail sent to "[email protected]" to "[email protected]" by changing the header information. That would explain the lack of e-mail address preservation in the header I think.
Actually re-reading your question I see that you set up the new account/alias in the same way you set up your matt.simmons alias, but it didn't work on the new account. I guess the questions I have is what level of access do you have to the Exchange server itself and what level of control do you have in the account/alias creation? Are you sure that both accounts reside on the same Exchange server? Since it is hosted they may not and there may be something funky set up on the server that the new account is on...
The best option is to setup a separate email account but if you do not want to do that you may also want to check on which program is being used to send the email and make sure that is not a problem? Is it being sent internally or from an external user? Do you know which version of exchange? Have you spoken with Apptix Support?
Have you tried re-creating the account & Alias to clear out anywhere it might be cached.