I'm getting the same errors, and only when I send email to yahoo.com:
1/13/2024 3:53:26 PM - Server at MN2PR13MB3870.namprd13.prod.outlook.com returned '550 5.4.300 Message expired -> 421 4.4.2 Connection dropped due to SocketError'
1/13/2024 3:52:24 PM - Server at mta5.am0.yahoodns.net (67.195.228.106) returned '421 4.4.2 Connection dropped due to SocketError'
I'm on Office Pro Plus 2016 using the desktop client, although it happens from the web client as well. My account is Microsoft 365 Business Basic.
I've tried sending to two different yahoo.com emails and I have sent at least 5 emails over 2 days.
The support article you listed presumes I'm using an old TLS version, but I'm using whatever Microsoft 365 supplies by default. Based on the fuller headers below, it's all TLS 1.2.
Original message headers:
Received: from CH0PR13MB5082.namprd13.prod.outlook.com (2603:10b6:610:ed::14)
by MN2PR13MB3870.namprd13.prod.outlook.com (2603:10b6:208:1e9::20) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.7181.21; Sat, 13 Jan
2024 13:59:18 +0000
Received: from MW5PR13MB5878.namprd13.prod.outlook.com (2603:10b6:303:1c9::5)
by CH0PR13MB5082.namprd13.prod.outlook.com (2603:10b6:610:ed::14) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.7181.21; Sat, 13 Jan
2024 02:55:19 +0000
ARC-Seal: i=1; a=rsa-sha256; s=arcselector9901; d=microsoft.com; cv=none;
b=DGeCf6TtbQRfJoqXMvaTrygs8ztPaSTX7pbbh7640MhFEsqRvZm5inAXsZ0aBCD0yqCPZ9vl+u+XzfSHdIm0B8xqfppBHPC0aqlDpDDZDAkF6ygttBjE2efHBCoyANaXLbsHC4VLOxZC8ve5v2AB8IEiUoIWxV7tAEyEsBAbn1jce4FTAC02ZgP0IAR16jFr36tlznqlt/F6tevE3uXI16GSGcu79YqM1oBmIeAqCQ5GAyliiz+PGrxvEDmqikuySULaZcoxt4gWlifNt/qn1GBxmQHEszveRzu2EKRkqkSzZ04ltElEb2hodRET+iEruR0YJMdWLJJGXreZhk1Tbw==
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=pmF0dHM+eqWtinvkBnN3FlkywqX3KfqXGO+QxEwFxAU=;
b=Ifx401K/pquhV5LSao1qwLLDqDtd/Coitmvtb4jbeoMBQspquKabvFMTBcSeHMIkR5wr1nci+ZPP6vJ1hj/PEryFmNzYC7kOEIxp+a/ryXK9BYA8ScJzzPfu+P6Cr0YeDCVGvAOV6cEnzFX+93VGG4fGUtq8sAdVIL6ZIqnU9Y6pSuH6GGcJwHRIvDYFqBnM3jzPUU62s3i6DUQCfDFpkBc07xBoLB01jf7XG1wmFLfUkxLJ1C5RisSjTTER/TBZTZ1WESPJl4yj6rGU79jaYRuQirDU22XVUCdtU01jratZ8v0gdXkoRLVd2NaCfbCvpmHHNo5DCvT559MihRX7Tw==
ARC-Authentication-Results: i=1; mx.microsoft.com 1; spf=pass
smtp.mailfrom=larryseltzer.com; dmarc=pass action=none
header.from=larryseltzer.com; dkim=pass header.d=larryseltzer.com; arc=none
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
d=LarrySeltzer.onmicrosoft.com; s=selector2-LarrySeltzer-onmicrosoft-com;
h=From:Date:Subject:Message-ID:Content-Type:MIME-Version:X-MS-Exchange-SenderADCheck;
bh=pmF0dHM+eqWtinvkBnN3FlkywqX3KfqXGO+QxEwFxAU=;
b=J6KTBOxh8gd/9BVQ1o4Wiz88qYhal/bam0GgmbrLfOn6jN0+ZSnl9OwnCa2Nbf5VcEFPgUfiJ6ksMpUPwYY//J0jIR9N1qEecNNUOPOcd3X7SVT8v0Mqqdf7KDZXyCzuY+vei2I+dRbG7yxZRHj72HAJzOGvi1lE9BikQQidIbw=
Received: from BLAPR13MB4578.namprd13.prod.outlook.com (2603:10b6:208:332::10)
by MW5PR13MB5878.namprd13.prod.outlook.com (2603:10b6:303:1c9::5) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.7181.18; Fri, 12 Jan
2024 15:52:35 +0000
Received: from BLAPR13MB4578.namprd13.prod.outlook.com
([fe80::bfc2:9102:248f:3ec9]) by BLAPR13MB4578.namprd13.prod.outlook.com
([fe80::bfc2:9102:248f:3ec9%5]) with mapi id 15.20.7181.018; Fri, 12 Jan 2024
15:52:35 +0000
From: Larry Seltzer <******@larryseltzer.com>
To: Miranda Aaron <******@yahoo.com>
Subject: RE: did you get this?
Thread-Topic: did you get this?
Thread-Index: AQHaRW8l29TU3qmeL0CC3dpEwkx787DWU56g
Date: Fri, 12 Jan 2024 15:52:35 +0000
Message-ID: <******@BLAPR13MB4578.namprd13.prod.outlook.com>
References: <******@mail.gmail.com>
<******@yahoo.com>
In-Reply-To: <******@yahoo.com>
Accept-Language: en-US