SMTP Account Not Used

Question asked by Stratos Geroulis - 5/17/2017 at 7:10 AM

Unanswered

Hello,

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 mail.acme.com). 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 me@acme.com 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 mail.acme.com sent the email from me@acme.com.

That has not been my experience (and I just noticed). When I set my send from field to be me@acme.com and I check the raw message on the receiving side I see:

Received: from personal.com (personal.com. [xxx.xxx.xxx.xxx])

rather than

Received: from acme.com (acme.com. [yyy.yyy.yyy.yyy])

Moreover the return path of the message is:

Return-Path: <me@personal.com>

rather than

Return-Path: <me@acme.com>

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 me@acme.com 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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Larry Duran Replied

5/17/2017 at 10:43 AM

Employee Post

Hello Stratos, have you tried following the KB article to see if maybe you missed something? The KB article can be found here, http://portal.smartertools.com/kb/a3007/send-and-receive-email-from-third-party-accounts.aspx.

I just added my GMail account to my SmarterMail 16 account and I'm able to send emails through SmarterMail with my GMail account so the functionality should work.

Larry Duran Software Developer SmarterTools Inc. www.smartertools.com

Stratos Geroulis Replied

5/17/2017 at 10:50 AM

Hello, thank you for the response.

Yes, that's pretty much what I did. And it does work, it does send an email that when someone receives it it says "me@acme.com". But, the header is a little wonky. As I mentioned, even when I receive the email and check the header, the SMTP I have dedicated (mail.acme.com) is nowhere to be found on the server trace (received from). What Smartermail actually appears to be doing is that it uses it's own SMTP and sends the email directly. This behavior, strict servers (as I understand it), do not tolerate it i.e. sending an email with a different address than the SMTP you're using.

I'm not sure if I'm missing something here...

Stratos Geroulis Replied

5/17/2017 at 10:56 AM

Here's a sanitized example:

Delivered-To: me@gmail.com
Received: by 10.79.146.22 with SMTP id [.......]
        Wed, 17 May 2017 06:45:53 -0700 (PDT)
X-Received: by 10.31.114.66 with SMTP id [........]
        Wed, 17 May 2017 06:45:53 -0700 (PDT)
[...]
Return-Path: <me@personal.com>
Received: from personal.com (personal.com. [xxx.xxx.xxx.xxx])
        by mx.google.com with ESMTP id [........]
        for <me@gmail.com>;
        Wed, 17 May 2017 06:45:52 -0700 (PDT)
Received-SPF: pass (google.com: domain of me@personal.com designates xxx.xxx.xxx.xxx as permitted sender) client-ip=xxx.xxx.xxx.xxx;
Authentication-Results: mx.google.com;
       spf=pass (google.com: domain of me@personal.com designates xxx.xxx.xxx.xxx as permitted sender) smtp.mailfrom=me@personal.com
From: Stratos Geroulis <me@acme.com>
To: "me@gmail.com" <me@gmail.com>
Subject: test3
Date: Wed, 17 May 2017 13:45:46 GMT
Reply-To: me@acme.com
Message-ID: <[....]@personal.com>
MIME-Version: 1.0

See how mingled the info is? It says that the email is coming from "me@acme.com" but server "personal.com" 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...

Larry Duran Replied

5/17/2017 at 4:34 PM

Employee Post

I have my GMail account connected to my SmarterMail account and I was able to send an email to my Yahoo account and it looks like this:

Return-Path: <me@smartertools.com>
From: "me@gmail.com" <me@gmail.com>
To: "LARRY DURAN" <me@yahoo.com>
Subject: Test my SMTP account
Date: Wed, 17 May 2017 23:15:24 GMT
Reply-To: me@gmail.com

From what I can tell it looks similar to your raw email contents. I'm not sure if it relays the email to the STMP server or if it sends the email on behalf of the SMTP server, but it looks like it's working correctly.

Larry Duran Software Developer SmarterTools Inc. www.smartertools.com

Stratos Geroulis Replied

5/18/2017 at 5:15 AM

Thanks for sticking with it and running the test.

As you can see, the return path should not be "me@smartertools.com" it should be "me@gmail.com". Also, if you check the headers a little further, you will be able to tell if Smartermail bypassed the GMail SMTP (which it shouldn't if it works as expected). You can check for the header "Received: by [...]". This will tell you which SMTP server relayed the email to Yahoo.

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