Link to home
Start Free TrialLog in
Avatar of xmi
xmiFlag for Belgium

asked on

Mac Mail: how to send from multiple Exchange aliases ?

Customer is using Office 365 as backend and uses several domains:,, etc.

Each user has one mailbox and assigns multiple aliases/addresses to that mailbox:,, etc. Any mail sent to any of the aliases ends up in the user's mailbox, fine.

On the client side, users are using Macs with the built-in Mac Mail application.  The users must be able to select the alias they want to use as sender's email address. How can this be achieved ?

Things tried that did not work: adding the aliases into the account preference (you can then select an address to send from, however emails always appear to come from the default address), using shared mailboxes for the additionnal email adresses and access them via IMAP (sending works but emails are downloaded multiple times, a sending only IMAP account would be nice)

Any help would be appreciated.
Avatar of strung
Flag of Canada image

I am assuming it is the "reply to" address you want to be able to change.

To do that, in Mail go to Mail > Preferences > Accounts > Account Information

In the box "E-mail address" enter all the e-mail addresses you might want to use as Reply To addresses separated by commas.

Save the preferences, then quite and restart mail.

When you compose a mail message, click on the "From" box and you should be presented with a drop-down box allowing you to select among the E-mail addresses you put into the prefs box.
Avatar of xmi


I already tried that, it does not work. While I am able to select an email adress when I compose the message, it is always the first address that get's assigned as reply-to.

My assumption here is that the client does not communicate well with the Exchange BackEnd and that it is always the Office 365 / Active Directoy UPN that is used as reply-to.
You may be right. It seems to work with IMAP accounts and unfortunately, I don't have an exchange account to test.
Avatar of Will Szymkowski
You can ONLY have one Primary SMTP address. This is the only address you can send from Alias are only for receiving mail not sending.

Avatar of xmi
Flag of Belgium image

Link to home
This solution is only available to members.
To access this solution, you must be a member of Experts Exchange.
Start Free Trial
Avatar of xmi


Self answered the question after some testing.