SMTP Account Not Used
Question asked by Stratos Geroulis - May 17, 2017 at 7:10 AM
I have a question about something that I might actually be understanding or doing wrong. Here's what I have.
I have a mail server setup using Smartermail 16 for my personal emails on my personal server. I have also set it up to pickup my work's emails as well with a POP account (let's call it Since I want to be able to send emails from my work email address through my server I have also setup an SMTP connection to the same server.
Now, when I send an email from my work account, say through Smartermail I would expect my Smartermail server to connect to that SMTP and relay that email. So, the receiving end should actually see that sent the email from
That has not been my experience (and I just noticed). When I set my send from field to be and I check the raw message on the receiving side I see:
Received: from ( [])
rather than
Received: from ( [yyy.yyy.yyy.yyy])
Moreover the return path of the message is:
Return-Path: <>
rather than
Return-Path: <>
Now, maybe I don't really understand how it is supposed to work and it is actually doing what it's supposed to be doing but I have seen that when the receiving end gets an email from but it's coming from a different server (and the return path is also different) it's bounced back (and from my understanding for good reason).
Sorry for the long message but I guess my question is is this supposed to happen? If this is by design, what I am trying to do (send email from my work address through my personal Smartermail server and make it seamless like it was sent from outlook or something) is it even possible?
Thanks for your time and help!

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Here's a sanitized example:
Received: by with SMTP id [.......]
        Wed, 17 May 2017 06:45:53 -0700 (PDT)
X-Received: by with SMTP id [........]
        Wed, 17 May 2017 06:45:53 -0700 (PDT)
Return-Path: <>
Received: from ( [])
        by with ESMTP id [........]
        for <>;
        Wed, 17 May 2017 06:45:52 -0700 (PDT)
Received-SPF: pass ( domain of designates as permitted sender);
       spf=pass ( domain of designates as permitted sender)
From: Stratos Geroulis <>
To: "" <>
Subject: test3
Date: Wed, 17 May 2017 13:45:46 GMT
Message-ID: <[....]>
MIME-Version: 1.0
See how mingled the info is? It says that the email is coming from "" but server "" sent it. If I'm not mistaken, this is a flag for spam filters, is it not?
I hope I'm not being a pain...

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