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So I have a personal email account personal@domain.com
This email is a catch all address for the domain, setup on a Linux server using postfix/dovecot (IMAP/SMTP). I never share the email directly with anyone, and different people have different aliases. Under Thunderbird, this works great, I can choose any custom "FROM" address, postfix will never complain that this FROM address is different from the authenticated smtp address, and no trace of the real address is present anywhere in the headers.
Outlook on the other hand.. Just can't get its head around the concept, and I don't see how I can do that.
When I send an email from "alias1@domain.com" using outlook, the email will contain a "sender:" header which is "personal@domain.com", completely defeating the purpose. A simple header_checks in Postfix removed this "sender:" header, but there is also the first "MAIL FROM:" command which is personal and not the alias.
So my question is one of two.
1) Can I get Outlook to understand I really really want only the alias to show up and for all intents and purposes show up as if it's a real email (Just like Thunderbird handles it)?
I don't mind any level of Outlook hacking, and if I have to dabble with some VB to do it, I won't mind, just point me to some resources of how I can on-the-fly modify an email being sent.
2) Can I do it in Postfix? I tried this in header_checks:
/^Sender:/ IGNORE
/^MAIL\ FROM:\ <personal@domain.com>/ REPLACE MAIL FROM: <xxxxxxxxx@domain.com>
The first line successfully removes the Sender header (Which has the horrible effect of displaying "From XX on behalf of YY"), but the second one is not catching the other instances of personal appearing in headers, namely "MAIL FROM:" which is then translated to "Return Path".
Any pointers appreciated.
How exactly do you set the "From" field in Outlook? – thims – 2017-05-19T17:21:52.900
@thims depends on Outlook version, but in the mail compose window, under the Options tab, you can enable editing the "From:" field. In newer Outlook, it's enabled by default, you click on "From:" and edit it. – Waleed Hamra – 2017-05-20T20:02:49.853