Gmail is junking e-mails originated from Spamgourmet

General discussion re sg.

Gmail is junking e-mails originated from Spamgourmet

Postby VanguardLH » Fri Sep 04, 2015 12:59 am

I wanted to test if Microsoft (Hotmail/Live/ had gotten around to accept "#" in the left token (username) portion of an e-mail (so I could reply to SG aliased e-mails to go back through SG to keep the alias intact). See my prior discussion at:


Well, looks like I can send e-mails to recipients with "#" in the left token (which SG uses to differentiate the recipient from the alias they used). I sent a test message from my Hotmail account to my Gmail account. Hotmail did not complain this time about invalid syntax for the left token, so the e-mail got sent. The test e-mail also arrived in my Gmail account so the test worked except that Gmail flags e-mails from SG as spam. Instead of my test e-mail going into my Gmail's Inbox, it was instead in Gmail's Spam folder. When I review the test message in Gmail's Spam folder, there is a yellow infobar saying:

Why is this message spam? It is a violation of Google's recommended email sender guidelines.

They don't like e-mails originating from SG. In their infobar, they provide the following hyperlink:
(I won't duplicate the article here.)

When I look at the received test e-mail junked into Gmail's spam folder, the headers are:

Code: Select all
Delivered-To: {me}
Received: by with SMTP id 137csp24482itv;
        Thu, 3 Sep 2015 17:26:02 -0700 (PDT)
X-Received: by with SMTP id qv2mr1698757pbc.6.1441326362857;
        Thu, 03 Sep 2015 17:26:02 -0700 (PDT)
Return-Path: <>
Received: from ([2607:ff10:c5:506:225:90ff:feab:5c2e])
        by with ESMTPS id ox10si990362pdb.187.2015.
        for <{me}>
        (version=TLS1_2 cipher=AES128-SHA256 bits=128/128);
        Thu, 03 Sep 2015 17:26:02 -0700 (PDT)
Received-SPF: temperror ( error in processing during lookup of DNS error) client-ip=2607:ff10:c5:506:225:90ff:feab:5c2e;
       spf=temperror ( error in processing during lookup of DNS error) smtp.mailfrom=
Received: from spamgourmet by with local (Exim 4.80)
   (envelope-from <{sgalias}>)
   id 1ZXepO-00034r-06
   for {me}; Fri, 04 Sep 2015 00:26:02 +0000
Received: from ([])
   by with esmtp (Exim 4.80)
   (envelope-from <{sgalias}>)
   id 1ZXepN-00034h-P1
   for ; Fri, 04 Sep 2015 00:26:01 +0000
Received: from BLU173-W36 ([]) by over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23008);
    Thu, 3 Sep 2015 17:26:00 -0700
X-TMN: [h1YW9dR5vg8trho2uWPTufoAMBDn7bXW]
X-Originating-Email: [{sgalias}]
Message-ID: <BLU173-W36154A47B13B3C5E3227ABF8570@phx.gbl>
Content-Type: multipart/alternative;
From:  {sgalias}
To:  {me}

I noticed the Return-Path header is null instead of pointing back to my SG alias. My understanding is that denotes the recipient cannot (should not) reply to the e-mail as the reply will be undeliverable. Bulk mailers do that so recipients don't reply to a non-listening server. The Received header showing SG connecting and sending to Hotmail is okay but before that was the Received-SPF header showing Google doesn't like or cannot retrieve SG's SPF record, or SG's SPF record is invalid.

Hotmail accepted an e-mail with "#" in the left token of the recipient's e-mail address so I could now have SG point to Hotmail to receive aliased e-mails and even reply to them. A Received header shows Hotmail connected okay to SG. While there is a valid Received header for SG connecting to Gmail, there is also the SPF error which has Gmail junking my reply message.

If the aliased sender were a Gmail user, it is unlikely they will see my reply to them since Gmail is dumping my reply in the Spam folder due to something they do not like about SG's SMTP service. There are a lot of Gmail users so it is far from rare that I will reply to an SG aliased message originating from a Gmail user.
Yes, I can define rules in my Gmail account to prevent SG aliased e-mail replies from ending up in the Spam folder. That does nothing for the recipient's (original senders) to whom I reply using the alias.

So now Hotmail will accept "#" in the left token of an e-mail address. I can reply to an SG aliased e-mail from a Hotmail account. Alas, Google has decided they don't like Spamgourmet or they don't like the SPF record in SG's nameserver. I used to do a lookup on SG's SPF record for hostname They report there are no SPF records in your nameserver. So why would Gmail be complaining about a problem with an SPF record when you don't have one?

Is it because I have always used for the right token of my alias e-mail addresses but SG is sending from (i.e., the domains do not match)? If SG is not publishing an SPF record then I do not see how that would matter.
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