Outlook rules - Emails sent from within my exchange server are unaffected

Question

On an Exchange server, I have an email address, email@domain.com. For this same address, I have an alias set up, which is test@domain.com. My goal is to have multiple alias for this address, and the same number of folders. test@domain.com will have folder "Test", test2@domain.com will have "Test2", etc

Pretty simple configuration.

I have setup a rule that checks the recipient of an email. If it is test@domain.com, it will be moved to the "Test" folder, etc... But this does not work. The alias are converted to "email@domain.com" before the rule can be processed, and emails end up in every folder that has a rule setup.

I tried another rule, which searches the email header for a specific word. The word is the alias, so "test@domain.com". If it finds the word the email is moved to the folder. This works perfectly if I send the email from an address that is hosted outside of the exchange server, in my case a gmail address. But when I send it from an address hosted withtin my exchange server, the rule doesn't work and the message is not moved to the folder.

I have removed the alias and the address email@domain.com from my GAL, but the problem remains. Does Exchange convert an alias to its matching email before sending a message? Hence why Outlook cannot find a trace of it in the message header?

Thank you

Answer 1

Your Exchange Server resolves any alias into a primary email. This is how it works and you can't change it.

What you can do is to use some kind of workaround. For example, in my company we're using Mail Contacts instead of email aliases. This allows us to send as any required contact and to correctly route email using Exchange Transport Rules.