Gmail deliverability issue when MIAB setup as a relay

[torch2k]

Scenario:

mail.siteservice.net (Server 1) is a fresh MIAB install.
A new user account and DNS entries are all setup correctly.

vps1.mediaserve.ca (Server 2) is a standard web server setup.
Postfix has been configured to use Server 1 as an SMTP relay using sasl as outlined here

Emails are getting through to Gmail but ending up in spam even though Gmail is giving it a “PASS” grade. Raw headers below. Can anyone provide some help/insight? Thanks.

ARC-Authentication-Results: i=1; mx.google.com;
       spf=pass (google.com: domain of torch@vps1.mediaserve.ca designates 134.209.39.167 as permitted sender) smtp.mailfrom=torch@vps1.mediaserve.ca
Return-Path: <torch@vps1.mediaserve.ca>
Received: from mail.siteservice.net (mail.siteservice.net. [134.209.39.167])
        by mx.google.com with ESMTPS id n58si24466845qtk.31.2019.10.16.12.48.56
        for <phil@w3dev.ca>
        (version=TLS1_3 cipher=TLS_AES_256_GCM_SHA384 bits=256/256);
        Wed, 16 Oct 2019 12:48:56 -0700 (PDT)
Received-SPF: pass (google.com: domain of torch@vps1.mediaserve.ca designates 134.209.39.167 as permitted sender) client-ip=134.209.39.167;
Authentication-Results: mx.google.com;
       spf=pass (google.com: domain of torch@vps1.mediaserve.ca designates 134.209.39.167 as permitted sender) smtp.mailfrom=torch@vps1.mediaserve.ca
Received: from authenticated-user (mail.siteservice.net [134.209.39.167]) (using TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)) (No client certificate requested) by mail.siteservice.net (Postfix) with ESMTPSA id 60FCF827A0 for <phil@w3dev.ca>; Wed, 16 Oct 2019 15:48:56 -0400 (EDT)
Received: from authenticated-user (mail.siteservice.net [134.209.39.167]) id C5264BD121; Wed, 16 Oct 2019 19:48:54 +0000 (UTC)

[alento]

Content perhaps?

Have you sent the same content to mail-tester.com? If so, what were the results?

[torch2k]

The content is just along the lines of a Wordpress test email.

I didn’t know about that site, looking into it now - it only scored a 6.5/10.

[alento]

@torch2k

I didn’t know about that site, looking into it now - it only scored a 6.5/10.

That is a problem … check that sites recommendations and make the changes suggested, or if you have questions, PM me the link and I will see what the issues are and translate if needed.

[torch2k]

Unfortunately i’m not able to PM yet, but I would appreciate you checking it out. The test email had some bad mime headers so it now scores an 8.3. Here is the link.

There is a Barracuda issue that I’ve already submitted a request on. I would love to know how to tell my Ubuntu Postfix to use the DKIM signature from MIAB?