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
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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.
>
> _______________________________________________
> mailop mailing list
> mailop@mailop.org
> https://list.mailop.org/listinfo/mailop
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------------------------------

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