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I'm having problems with delivery of emails from an application on a web server to Gmail. Gmail is displaying a round circle with a question mark, instead of the first letter of the sender, and hovering over it gives the message in this post's title.

Here is the setup: my client, ClientSite.ie is hosted on my web server, webserver.net. The site ClientSite.ie is a jobs board and users can sign up to receive alerts of new jobs by email, for example I'm signed up with myself@gmail.com. So when I get my job alert email at myself@gmail.com I'm seeing (?) instead of (C) beside the subject line within Gmail.

Two other points:

The MX for ClientSite.ie is handled by outlook.com (using some Microsoft business email product, which I can't remember the name of) - this is used for the human generated, general businesses email. The email described here is send from webserver.net via PHP and database queries.

For bounce processing I'm using VERP. Because the MX for MyClientSite.ie is hosted by Microsoft, I'm using a domain belonging to me (my_own_domain.info), and hosted on webserver.net to filter bounces to a PHP file using qmail.

Return-Path: <alertsbounce-69283.7384.myself_gmail_com@my_own_domain.info> - unique to each recipient.

When I click in the question mark in gmail, it leads to a page which suggests SPF should be enough to authenticate.

I have an SPF:

v=spf1 mx a a:webserver.net include:outlook.com include:my_own_domain.info ~all

Google also says DKIM will work, but if I can get by with SPF that would be great!

Thank you.

Full headers

Delivered-To: myself@gmail.com
Received: by 2002:a05:6504:149a:0:0:0:0 with SMTP id m26csp31322lto;
        Thu, 19 Mar 2020 17:16:16 -0700 (PDT)
X-Google-Smtp-Source: ADFU+vsh1ckhIK3EGN0mbfVeh4LoXgqsZwJqhrrDphamwG5oYCPEAYTuj1RzNEJNnoZvv6H0vusx
X-Received: by 2002:aed:2f25:: with SMTP id l34mr5253892qtd.99.1584663376615;
        Thu, 19 Mar 2020 17:16:16 -0700 (PDT)
ARC-Seal: i=1; a=rsa-sha256; t=1584663376; cv=none;
        d=google.com; s=arc-20160816;
        b=i4JxQA7AhD/OVr8LLhFaK/QszWNh1t8cdqdNggL76Ql+XswSTUma41xmRWjcz2xgfh
         yUzvvtotKRyqrsA/K0AvwwrEvy+jNYsHOv0wSNlXwL9RMUI4hPBuxEy/3sSyInHYx4Ac
         p1amILVhHvhhzOxf198Fo4tHpON/GM1y+ISsHi4WBJSQ5tQYyOUp66WuMnaFkz6DKq4+
         R7Ep4VJdqHRCdRfKEYfj8HHyqYnxpxZHPWTD9vf8ZlUTk4FbUJQX+wZMNIOEVj5GjKY5
         Fsm/1b9E/b3TYAxFtc3qQvk9e+N9x/5fq0LJfTgqQGzh8kvoycv0zOVjc78H6m7WuqBu
         fTog==
ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
        h=content-transfer-encoding:mime-version:message-id:subject:from:to
         :date;
        bh=xElb1IJMQt0e7hsiYeCPwyCla6oTNyyIK4tca7ucCoM=;
        b=CDYJefZRx3DfTHIdZyCWyaYmY57LVIvuvvJrHcXeyjYneQI0ooSCl7hTYiQNOEu/T0
         uJaTa4oW7fAH6B0ZCv/JcJYb3UqFvIStjGvMFD9/cIbVzTxY70mzindAz6OyEMi6FJyQ
         Vo3QZfNxj63Z6lGWC8yIOWfufGBIMYNT3acYuupigWp66jzXCgdYyG43CL49w/W1nKiv
         G0n8e2LiVQIVgYON6lr45EOWyelpACkjYFM6qdgCb4aqYjH3m1TPssICjY+qRwDdM1Wb
         udBI14SNQHcLF6MagBg65UbCkCJYFLFnpvXpGQjMgjJWLf+q9y9I+ShrFxZRwyRlRNb3
         CJrQ==
ARC-Authentication-Results: i=1; mx.google.com;
       spf=neutral (google.com: 2607:f440::d85c:7f52 is neither permitted nor denied by best guess record for domain of alertsbounce-69283.7384.myself_gmail_com@my_own_domain.info) smtp.mailfrom=alertsbounce-69283.7384.myself_gmail_com@my_own_domain.info
Return-Path: <alertsbounce-69283.7384.myself_gmail_com@my_own_domain.info>
Received: from webserver.net ([2607:f440::d85c:7f52])
        by mx.google.com with ESMTPS id q7si2194777qvo.58.2020.03.19.17.16.16
        for <myself@gmail.com>
        (version=TLS1_2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128);
        Thu, 19 Mar 2020 17:16:16 -0700 (PDT)
Received-SPF: neutral (google.com: 2607:f440::d85c:7f52 is neither permitted nor denied by best guess record for domain of alertsbounce-69283.7384.myself_gmail_com@my_own_domain.info) client-ip=2607:f440::d85c:7f52;
Authentication-Results: mx.google.com;
       spf=neutral (google.com: 2607:f440::d85c:7f52 is neither permitted nor denied by best guess record for domain of alertsbounce-69283.7384.myself_gmail_com@my_own_domain.info) smtp.mailfrom=alertsbounce-69283.7384.myself_gmail_com@my_own_domain.info
Received: by webserver.net (Postfix, from userid 89526) id 35C083060D88; Fri, 20 Mar 2020 00:11:06 +0000 (GMT)
Date: Fri, 20 Mar 2020 00:10:12 +0000
To: myself@gmail.com
From: "MyClientSite.ie Job Alert" <alerts@MyClientSite.ie>
Subject: Job alerts for Kevin
Message-ID: <35a2f807ca908402f35008c834e1bc06@webserver.net>
X-Mailer: PHPMailer 5.2.22 (https://github.com/PHPMailer/PHPMailer)
MIME-Version: 1.0
Content-Type: text/html; charset=UTF-8
Content-Transfer-Encoding: 8bit
KevInSol
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1 Answers1

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This is fixed now thanks to help elsewhere.

Turned out the SPF was not valid because I had no SPF in the domain used for the VERP return address (my_own_domain.info).

Adding v=spf1 mx a a:webserver.net ~all fixed it.

I also removed reference to my_own_domain.info in the ClientSite.ie SPF.

Perhaps either actions would have done the job, but in the interests of expediency I just did both.

KevInSol
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