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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