Hi Mark,

I saw this and your test from the loopback. Everything looked good from ARC/DKIM/SPF/DMARC.  We've been seeing Google requiring DKIM authentication lately so we wanted to confirm that wasn't the issue.

Are you sending bulk emails? I noticed it's the BBB and they send a lot of messages people might mark as spam.

The error from Google says that their antispam system has marked it as spam.  Is there any content of note in your messages that are getting blocked?  Anything like links in a signature to URLs that might be in a blocklist?

One thought to get that escalated is to email a Google Workspace paying customer and have them make a support request about the issue.

Regards,

KAM


On 10/26/2023 4:07 PM, Mark Stanley via mailop wrote:
RAPTOR REMARK: Alert! Please be careful! This email is from an EXTERNAL sender. 
Be aware of impersonation and credential theft.

KAM - I sent a message as one of my users to that email address you supplied 
and listed below is the bounceback message we get:

More Info for Email Admins
Status code: 550 5.7.350

When Office 365 tried to send the message to the recipient (outside Office 
365), the recipient's email server (or email filtering service) suspected the 
sender's message is spam.

If the sender can't fix the problem by modifying their message, contact the 
recipient's email admin and ask them to add your domain name, or the sender's 
email address, to their list of allowed senders.

Although the sender may be able to alter the message contents to fix this 
issue, it's likely that only the recipient's email admin can fix this problem. 
Unfortunately, Office 365 Support is unlikely to be able to help fix these 
kinds of externally reported errors.

Original Message Details
Created Date:   10/26/2023 8:05:05 PM
Sender Address: ba...@richmond.bbb.org
Recipient Address:      markwstanley2...@gmail.com
Subject:        testing again

Error Details
Error:  550 5.7.350 Remote server returned message detected as spam -> 550 
5.7.1 [104.47.57.168 12] Our system has detected that this message is;likely 
unsolicited mail. To reduce the amount of spam sent to Gmail,;this message has 
been blocked. Please visit; 
https://support.google.com/mail/?p=UnsolicitedMessageError for more;information. 
m14-20020a5d4a0e000000b003296b69535csi124898wrq.495 - gsmtp
Message rejected by:    mx.google.com

Notification Details
Sent by:        BL3PR04MB8106.namprd04.prod.outlook.com

We experienced a brief respite from all this yesterday afternoon and all users 
could actively send to Google domains. As of about noon today, it started 
happening again.

Mark W. Stanley, Managed Services Engineer
Richweb, Inc.  /  mstan...@corp.richweb.com
O: 804-368-0421 X 120
richweb.com / hvens.com

-----Original Message-----
From: mailop <mailop-boun...@mailop.org> On Behalf Of mailop-requ...@mailop.org
Sent: Thursday, October 26, 2023 3:54 PM
To: mailop@mailop.org
Subject: [SUSPECTED SPAM] mailop Digest, Vol 39, Issue 48

Caution! This message was sent from outside your organization.

Send mailop mailing list submissions to
        mailop@mailop.org

To subscribe or unsubscribe via the World Wide Web, visit
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or, via email, send a message with subject or body 'help' to
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When replying, please edit your Subject line so it is more specific than "Re: 
Contents of mailop digest..."


Today's Topics:

    1. Re: Still Don't understand Google's relaying systems..
       Duplicate Return-Path, and other things.. (Atro Tossavainen)
    2. Re: [External] Need Help with Google Deliverability Issue
       (Kevin A. McGrail)


----------------------------------------------------------------------

Message: 1
Date: Thu, 26 Oct 2023 22:17:49 +0300
From: Atro Tossavainen <mail...@atrotossavainen.fi>
To: mailop@mailop.org
Subject: Re: [mailop] Still Don't understand Google's relaying
        systems.. Duplicate Return-Path, and other things..
Message-ID: <20231026191749.gq28...@dm7.infinitemho.fi>
Content-Type: text/plain; charset=iso-8859-1

They're a legit Google customer. What's there to marvel at?
https://developers.google.com/gmail/api/guides <- have a look.

--
Atro Tossavainen, Founder, Partner
Koli-Lõks OÜ (reg. no. 12815457, VAT ID EE101811635) Tallinn, Estonia tel. 
+372-5883-4269, https://www.koliloks.eu/


------------------------------

Message: 2
Date: Thu, 26 Oct 2023 15:43:53 -0400
From: "Kevin A. McGrail" <kevin.mcgrail-mai...@pccc.com>
To: mailop@mailop.org
Subject: Re: [mailop] [External] Need Help with Google Deliverability
        Issue
Message-ID: <726fd9fa-da01-4d35-b711-25bbd218a...@pccc.com>
Content-Type: text/plain; charset="utf-8"; Format="flowed"

Mark, was there a bounce message with any information?

Send a message to raptorloopb...@raptoremailsecurity.com and that will
tell you what that spam scanner sees to check your SPF, DKIM, DMARC, etc.

Regards,
KAM

On 10/26/2023 3:13 PM, Mark Stanley via mailop wrote:
I have recently migrated one of our customers from Google to Office365
and have been encountering deliverability issues when sending to Google

Raptor Remark: Please be careful! This email is from an EXTERNAL
sender. Be aware of impersonation and credential theft.

I have recently migrated one of our customers from Google to Office365
and have been encountering deliverability issues when sending to
Google-related domains. All other domains are perfectly fine and
haven’t seen any issues. Listed below are the headers for a bounced
email to a Gmail account:

ARC-Seal: i=2; a=rsa-sha256; s=arcselector9901; d=microsoft.com; cv=pass;

b=IUdOSeOS2v8fBqFRT+2+ob/64xDWHCrxU6br11+L6Gjlytj2kEMHoVq7TCpkgY1uKHg/IxVBQh1bpLReem8wfvKVM4ncibBVmls1IAmgt/fFxBThm7Vgfc3HZUlmk0NYy+0ifABUO8cVWXE9nz0/XyjTXfmI2lo0CX4Ysgk+mN5FxmFHz1yCDYJomM0k8Naxr7+nO8d9TC7TQ/U2QlH6aHfa2I+kHP/vxNAYPumA6At7aBtXh7o5ULqNt3LDrW/tTJua/8M6Z5KZccU2GHa/wlEaaEH4g9/cLSPGn28kDx5bj1j5jMdl7zXjnETZYymGCEKFJwJMOFecCl3kI4YX7g==

ARC-Message-Signature: i=2; a=rsa-sha256; c=relaxed/relaxed;
d=microsoft.com;

s=arcselector9901;

h=From:Date:Subject:Message-ID:Content-Type:MIME-Version:X-MS-Exchange-AntiSpam-MessageData-ChunkCount:X-MS-Exchange-AntiSpam-MessageData-0:X-MS-Exchange-AntiSpam-MessageData-1;

bh=U1XPevLPW3kgepb4RRUmQy20bmFrzeFdm+z8xjlDhQo=;

b=MveUHC2brc6+/jbu/Q1RrDABPlHSagEN1omoqqUmP04RPTk60M+AZtFEC2tF2LImub4A1RvvL/w9FjP+lysSfftGpywNPazJHaPgGiW44cqS2S84sGkJFDgHCivhnSfBKYBKHFGvAZhjYe16CXWERd//M0u/yGtTRPoG8J/OSKUcugiMpsburQ6ffOHOmRLERu+w8fBKn7A+4rwIDoKP2/efhZNJ7xQWk/Z6MAB32UXmxWPYOY+/kUMRyQ1Z5Sf2ZAT9MoRnVldID4W9HeGMA75Ticxl8Dt0e/Q+XoD4f7BEHKpwoznNEr9HSLNQXkQSbSuPharKncn3fZEyIbQh6A==

ARC-Authentication-Results: i=2; mx.microsoft.com 1; spf=pass (sender
ip is

198.154.181.224) smtp.rcpttodomain=gmail.com
smtp.mailfrom=richmond.bbb.org;

dmarc=pass (p=none sp=none pct=100) action=none
header.from=richmond.bbb.org;

dkim=pass (signature was verified) header.d=richmond.bbb.org; dkim=pass

(signature was verified)
header.d=mail-dkim-us-west-2.prod.hydra.sophos.com;

arc=pass (0 oda=1 ltdi=1 spf=[1,1,smtp.mailfrom=richmond.bbb.org]

dkim=[1,1,header.d=richmond.bbb.org]

dmarc=[1,1,header.from=richmond.bbb.org])

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=richmond.bbb.org;

s=selector1;

h=From:Date:Subject:Message-ID:Content-Type:MIME-Version:X-MS-Exchange-SenderADCheck;

bh=U1XPevLPW3kgepb4RRUmQy20bmFrzeFdm+z8xjlDhQo=;

b=IBp6WddL0tAEtjsUg9TLjHYmU5nmyIqGMASfttCAkZzzJQLOspzOwgifiLEXyz3lfCwmIC89UkBptAT4Z0p5sFvDUNDTtWkMoK5nPxNpjJAZenjDXSrwRfwcj0WOjcLV7VaIvVYyEs2Db+8tikyWrR2VJ2I9iNAYJkIWqwP50u9jcPYUj3FHKR44B7cxTz1VXeegS2RPjZ968HuIvKsGx6gKSgtWobvcPsYgNA3apo1BZ/Y+i3h7cGx1cdJJPED5uyyeIj8dZ/l28DoMSETkT29DVqCcKvgbVQUyM2URBFUgvksANuYRRjFcE119QOlQSsyGyl1ligENnsozK5MyYQ==

Received: from DM6PR07CA0095.namprd07.prod.outlook.com
(2603:10b6:5:337::28)

by CO6PR04MB8329.namprd04.prod.outlook.com (2603:10b6:303:134::10) with

Microsoft SMTP Server (version=TLS1_2,

cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6933.22; Thu,
26 Oct

2023 19:00:26 +0000

Received: from DS1PEPF0001708E.namprd03.prod.outlook.com

(2603:10b6:5:337:cafe::30) by DM6PR07CA0095.outlook.office365.com

(2603:10b6:5:337::28) with Microsoft SMTP Server (version=TLS1_2,

cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6933.19 via
Frontend

Transport; Thu, 26 Oct 2023 19:00:25 +0000

X-MS-Exchange-Authentication-Results: spf=pass (sender IP is
198.154.181.224)

smtp.mailfrom=richmond.bbb.org; dkim=pass (signature was verified)

header.d=richmond.bbb.org;dmarc=pass action=none

header.from=richmond.bbb.org;

Received-SPF: Pass (protection.outlook.com: domain of richmond.bbb.org

designates 198.154.181.224 as permitted sender)

receiver=protection.outlook.com; client-ip=198.154.181.224;

helo=mfod-usw2.prod.hydra.sophos.com; pr=C

Received: from mfod-usw2.prod.hydra.sophos.com (198.154.181.224) by

DS1PEPF0001708E.mail.protection.outlook.com (10.167.17.134) with Microsoft

SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id

15.20.6933.18 via Frontend Transport; Thu, 26 Oct 2023 19:00:25 +0000

Received: from ip-172-17-2-248.us-west-2.compute.internal
(ip-172-17-2-248.us-west-2.compute.internal [127.0.0.1])

     by mfod-usw2.prod.hydra.sophos.com (Postfix) with ESMTP id
4SGZqr6KmBzdZMC

        for <markwstanley2...@gmail.com>; Thu, 26 Oct 2023 19:00:24
+0000 (UTC)

X-Sophos-Product-Type: Mailflow

X-Sophos-Email-ID: 331699fdd3364172b148bf658ab8ad0a

Received: from NAM12-DM6-obe.outbound.protection.outlook.com

(mail-dm6nam12lp2169.outbound.protection.outlook.com [104.47.59.169])

(using TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits))

(No client certificate requested)

by mf-outbound-usu-west-2.prod.hydra.sophos.com (Postfix) with ESMTPS id

4SGZqq1wzhzRhQn

for <markwstanley2...@gmail.com>; Thu, 26 Oct 2023 19:00:23 +0000 (UTC)

ARC-Seal: i=1; a=rsa-sha256; s=arcselector9901; d=microsoft.com; cv=none;

b=kJDl3l74RdoxT1QOA0ix5VgwvFhYhqzcUgGkZr0vhcxIyulP8EGiqJBMBBHFnEBAvzwYh6Wl3yoAV1RR5U6jCUuNWAHYG6lqhXMRycSJXMZCbJGY+k8DMwhMVOY48VMec+GZ8SzQOfjzIzoZ3eF6eLKvgc9ZVRyIP4y5EV3oOxn1SXnNP4uXC9Y6X+FLUW00R/RTiHFPlytHt4hhEktZ/5bGIMHknGHbLhcfsulVbFAfDPxCuI0lqwkpTOrlX4EjOEI09nEXghzxBhAOUmLX4eFJBcRfzMlUDlriv6gyYniTKeOVNuwn7eOb6Smy4W7STqkRth8Z48BmFYVCcexKMw==

ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed;
d=microsoft.com;

  s=arcselector9901;

h=From:Date:Subject:Message-ID:Content-Type:MIME-Version:X-MS-Exchange-AntiSpam-MessageData-ChunkCount:X-MS-Exchange-AntiSpam-MessageData-0:X-MS-Exchange-AntiSpam-MessageData-1;

bh=U1XPevLPW3kgepb4RRUmQy20bmFrzeFdm+z8xjlDhQo=;

b=j2oLsbNnA/8EGoq5tIM6WVMrAI8PefNYnRWMOmg9EoJTFxXNOViT1vcYZ1Tv80gLv/WICsLnQTBQrxDExEwVBZ636+WRwdjj9vOo0Mh6+O/mt8PDPxGLP+DfAxi0O000rB7d0hsQ6gugFt17fTwmrY7shWwVS94HM1SYFtcwpAJgeWLMJhgBrFCvWl1NzFtK7kLcmEzZL2RKCY+jy2MzFQMBJIcwM1G9pImeuxXM8evpuih/Q7GTnBivqS7Al2c4W0JnJCFoLopkJGYcTDddHPbg5PpopBWjR6UrbNXHvlCZeMsXXFQThIv9ZCcQnVgCHJZ4Ou84eskjk6eyRyQnbQ==

ARC-Authentication-Results: i=1; mx.microsoft.com 1; spf=pass

smtp.mailfrom=richmond.bbb.org; dmarc=pass action=none

header.from=richmond.bbb.org; dkim=pass header.d=richmond.bbb.org;
arc=none

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=richmond.bbb.org;

s=selector1;

h=From:Date:Subject:Message-ID:Content-Type:MIME-Version:X-MS-Exchange-SenderADCheck;

bh=U1XPevLPW3kgepb4RRUmQy20bmFrzeFdm+z8xjlDhQo=;

b=IBp6WddL0tAEtjsUg9TLjHYmU5nmyIqGMASfttCAkZzzJQLOspzOwgifiLEXyz3lfCwmIC89UkBptAT4Z0p5sFvDUNDTtWkMoK5nPxNpjJAZenjDXSrwRfwcj0WOjcLV7VaIvVYyEs2Db+8tikyWrR2VJ2I9iNAYJkIWqwP50u9jcPYUj3FHKR44B7cxTz1VXeegS2RPjZ968HuIvKsGx6gKSgtWobvcPsYgNA3apo1BZ/Y+i3h7cGx1cdJJPED5uyyeIj8dZ/l28DoMSETkT29DVqCcKvgbVQUyM2URBFUgvksANuYRRjFcE119QOlQSsyGyl1ligENnsozK5MyYQ==

DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/relaxed;
t=1698346819;

  s=v1; d=mail-dkim-us-west-2.prod.hydra.sophos.com;

h=Content-Type:Date:Subject:To:From;

bh=U1XPevLPW3kgepb4RRUmQy20bmFrzeFdm+z8xjlDhQo=;

b=jcJw6d6HDGLRjPmeM/Ye+DF43hHJMaao4by5+Jfi6F45SAggkc4D41+8pFSpNk2t

Qx7LNQOyPjHyJ4K1AqYgL973657era/YNEniTZsHKZS5CIyFqjxQBu73Uk0YkrXzw3W

L6oNeNo4Bp/kKYZXG8aKNFFBTUkea06TysmByIp4T+AiSUca1JkVpcciwzviaqhoc18

lP9L/2U/ORZUDEzh037Jmx0CKYP30w9Ry3fp9cYmfkGUSvY0lIu2fwa5mDodB65OWjp

uoIFFVzDGfpi28usziso1gO89Ih7n0MMIj6TTrGJx0ZzuxKXZilwUIg9zKNr8ey1Gka

LtUlmxEqag==

Received: from BY5PR04MB6706.namprd04.prod.outlook.com
(2603:10b6:a03:22e::24)

by MN2PR04MB7134.namprd04.prod.outlook.com (2603:10b6:208:1e3::24)

with Microsoft SMTP Server (version=TLS1_2,

cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6933.19; Thu,
26 Oct

2023 19:00:20 +0000

Received: from BY5PR04MB6706.namprd04.prod.outlook.com

([fe80::4324:9275:a4f7:113c]) by BY5PR04MB6706.namprd04.prod.outlook.com

([fe80::4324:9275:a4f7:113c%3]) with mapi id 15.20.6933.019; Thu, 26
Oct 2023

19:00:19 +0000

Any insight into this is greatly appreciated. We have getting bounce
backs for several days now, but experienced a brief period where
Google domains were able to be reached.

*Mark W. Stanley, Managed Services Engineer*

Richweb, Inc.  / mstan...@corp.richweb.com

O: 804-368-0421 X 120

richweb.com / hvens.com


RAPTOR REMARK: Alert! Please be careful! This email is from an EXTERNAL sender. 
Be aware of impersonation and credential theft.

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