SMTP does not work

I am confirming that I used outlook web app to do the tests.

I just received error messages in my email about those attempts. Here is one of them:

Delivery has failed to these recipients or groups:

@hotmal.com (@hotmal.com)Your message wasn't delivered. Despite repeated attempts to deliver your message, the recipient's email system refused to accept a connection from your email system.

Contact the recipient by some other means (by phone, for example) and ask them to tell their email admin that it appears that their email system is refusing connections from your email server. Give them the error details shown below. It's likely that the recipient's email admin is the only one who can fix this problem.

For Email Admins
No connection could be made because the target computer actively refused it. This usually results from trying to connect to a service that is inactive on the remote host - that is, one with no server application running. For more information and tips to fix this issue see this article: https://go.microsoft.com/fwlink/?LinkId=389361

Diagnostic information for administrators:

Generating server: SJ1PR11MB6252.namprd11.prod.outlook.com
Receiving server: SJ1PR11MB6252.namprd11.prod.outlook.com

@hotmal.com
1/12/2023 2:36:56 PM - Server at SJ1PR11MB6252.namprd11.prod.outlook.com returned '550 5.4.316 Message expired, connection refused(Socket error code 10061)'
1/12/2023 2:26:43 PM - Server at hotmal.com (20.103.85.33) returned '450 4.4.316 Connection refused [Message=Socket error code 10061] [LastAttemptedServerName=hotmal.com] [LastAttemptedIP=20.103.85.33:25] [SmtpSecurity=-2;-2] SN1NAM02FT0003.eop-nam02.prod.protection.outlook.com'

Original message headers:

Received: from SJ0PR11MB5069.namprd11.prod.outlook.com (2603:10b6:a03:2ad::6)
 by SJ1PR11MB6252.namprd11.prod.outlook.com (2603:10b6:a03:457::21) with
 Microsoft SMTP Server (version=TLS1_2,
 cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.5986.18; Thu, 12 Jan
 2023 02:41:51 +0000
ARC-Seal: i=1; a=rsa-sha256; s=arcselector9901; d=microsoft.com; cv=none;
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Received: from SA1PR11MB6943.namprd11.prod.outlook.com (2603:10b6:806:2bc::16)
 by SJ0PR11MB5069.namprd11.prod.outlook.com (2603:10b6:a03:2ad::6) with
 Microsoft SMTP Server (version=TLS1_2,
 cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.5986.18; Wed, 11 Jan
 2023 14:36:09 +0000
Received: from SA1PR11MB6943.namprd11.prod.outlook.com
 ([fe80::7dd0:819:810:e6a1]) by SA1PR11MB6943.namprd11.prod.outlook.com
 ([fe80::7dd0:819:810:e6a1%6]) with mapi id 15.20.6002.013; Wed, 11 Jan 2023
 14:36:09 +0000
From: Sidney  <@hotmail.com>
To: "@hotmal.com" <@hotmal.com>
Subject: Quote 4470 
Thread-Topic: Quote 4470 
Thread-Index: AQHZJcoIvErYTgc2jU2MaA2rVYNJSQ==
Date: Wed, 11 Jan 2023 14:36:09 +0000
Message-ID: <******@SA1PR11MB6943.namprd11.prod.outlook.com>
Accept-Language: en-CA, en-US
Content-Language: en-CA
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
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x-tmn: [nWW1lDTd6/4BeJx7pwhC/rMtAAZNej5e]
x-ms-publictraffictype: Email
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SA1PR11MB6943:EE_|SJ0PR11MB5069:EE_|SJ1PR11MB6252:EE_
x-ms-office365-filtering-correlation-id: b3c78d96-df5f-45a2-4fb2-08daf3e12e19
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Content-Type: multipart/alternative;
boundary="_000_SA1PR11MB69437EB6EE4CD5430C925333B0FC9SA1PR11MB6943namp_"
MIME-Version: 1.0
X-MS-Exchange-CrossTenant-AuthAs: Internal
X-MS-Exchange-CrossTenant-AuthSource: SA1PR11MB6943.namprd11.prod.outlook.com
X-MS-Exchange-CrossTenant-RMS-PersistedConsumerOrg: 00000000-0000-0000-0000-000000000000
X-MS-Exchange-CrossTenant-Network-Message-Id: b3c78d96-df5f-45a2-4fb2-08daf3e12e19
X-MS-Exchange-CrossTenant-originalarrivaltime: 11 Jan 2023 14:36:09.2791
 (UTC)
X-MS-Exchange-CrossTenant-fromentityheader: Hosted
X-MS-Exchange-CrossTenant-id: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa
X-MS-Exchange-CrossTenant-rms-persistedconsumerorg: 00000000-0000-0000-0000-000000000000
X-MS-Exchange-Transport-CrossTenantHeadersStamped: SJ0PR11MB5069
Return-Path: ******@hotmail.com
X-OriginatorOrg: sct-15-20-4755-11-msonline-outlook-e8f36.templateTenant

Here is the last one. Doesn't make sense to me

Undeliverable: email not working To send this message again, click here. postmaster@outlook.comYou Delivery has failed to these recipients or groups:

@hotmal.com (@hotmal.com)Your message wasn't delivered. Despite repeated attempts to deliver your message, the recipient's email system refused to accept a connection from your email system.

Contact the recipient by some other means (by phone, for example) and ask them to tell their email admin that it appears that their email system is refusing connections from your email server. Give them the error details shown below. It's likely that the recipient's email admin is the only one who can fix this problem.

For Email Admins
No connection could be made because the target computer actively refused it. This usually results from trying to connect to a service that is inactive on the remote host - that is, one with no server application running. For more information and tips to fix this issue see this article: https://go.microsoft.com/fwlink/?LinkId=389361

Diagnostic information for administrators:

Generating server: CH3PR11MB7321.namprd11.prod.outlook.com
Receiving server: CH3PR11MB7321.namprd11.prod.outlook.com

******@hotmal.com
1/12/2023 2:58:49 PM - Server at CH3PR11MB7321.namprd11.prod.outlook.com returned '550 5.4.316 Message expired, connection refused(Socket error code 10061)'
1/12/2023 2:53:47 PM - Server at hotmal.com (20.103.85.33) returned '450 4.4.316 Connection refused [Message=Socket error code 10061] [LastAttemptedServerName=hotmal.com] [LastAttemptedIP=20.103.85.33:25] [SmtpSecurity=-2;-2] DM6NAM10FT019.eop-nam10.prod.protection.outlook.com'

Original message headers:

Received: from CY8PR11MB7799.namprd11.prod.outlook.com (2603:10b6:930:78::14)
 by CH3PR11MB7321.namprd11.prod.outlook.com (2603:10b6:610:150::9) with
 Microsoft SMTP Server (version=TLS1_2,
 cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.5986.18; Thu, 12 Jan
 2023 14:47:14 +0000
Received: from BL1PR11MB5430.namprd11.prod.outlook.com (2603:10b6:208:31e::24)
 by CY8PR11MB7799.namprd11.prod.outlook.com (2603:10b6:930:78::14) with
 Microsoft SMTP Server (version=TLS1_2,
 cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6002.13; Thu, 12 Jan
 2023 02:43:28 +0000
ARC-Seal: i=1; a=rsa-sha256; s=arcselector9901; d=microsoft.com; cv=none;
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Received: from SA1PR11MB6943.namprd11.prod.outlook.com (2603:10b6:806:2bc::16)
 by BL1PR11MB5430.namprd11.prod.outlook.com (2603:10b6:208:31e::24) with
 Microsoft SMTP Server (version=TLS1_2,
 cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6002.13; Wed, 11 Jan
 2023 14:38:06 +0000
Received: from SA1PR11MB6943.namprd11.prod.outlook.com
 ([fe80::7dd0:819:810:e6a1]) by SA1PR11MB6943.namprd11.prod.outlook.com
 ([fe80::7dd0:819:810:e6a1%6]) with mapi id 15.20.6002.013; Wed, 11 Jan 2023
 14:38:06 +0000
From: Sidney Beauchamp <******@hotmail.com>
To: "******@hotmal.com" <******@hotmal.com>
Subject: email not working
Thread-Topic: email not working
Thread-Index: AQHZJcpNU7SOYonNJU6VByymKhq2bg==
Date: Wed, 11 Jan 2023 14:38:06 +0000
Message-ID: <******@SA1PR11MB6943.namprd11.prod.outlook.com>
Accept-Language: en-CA, en-US
Content-Language: en-CA
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Content-Type: multipart/alternative;
boundary="_000_SA1PR11MB694315C1F75F72E6B14A97CFB0FC9SA1PR11MB6943namp_"
MIME-Version: 1.0
X-MS-Exchange-CrossTenant-AuthAs: Internal
X-MS-Exchange-CrossTenant-AuthSource: SA1PR11MB6943.namprd11.prod.outlook.com
X-MS-Exchange-CrossTenant-RMS-PersistedConsumerOrg: 00000000-0000-0000-0000-000000000000
X-MS-Exchange-CrossTenant-Network-Message-Id: 89429d76-9782-4702-476a-08daf3e173f0
X-MS-Exchange-CrossTenant-originalarrivaltime: 11 Jan 2023 14:38:06.4194
 (UTC)
X-MS-Exchange-CrossTenant-fromentityheader: Hosted
X-MS-Exchange-CrossTenant-id: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa
X-MS-Exchange-CrossTenant-rms-persistedconsumerorg: 00000000-0000-0000-0000-000000000000
X-MS-Exchange-Transport-CrossTenantHeadersStamped: BL1PR11MB5430
Return-Path: ******@hotmail.com
X-OriginatorOrg: sct-15-20-4755-11-msonline-outlook-e8f36.templateTenant

I just tried to send with Sage to my gmail account and it worked but when I send it to my hotmail account it fails.

How can I escalate this issue ?

Well I'm not alone.

https://answers.microsoft.com/en-us/outlook_com/forum/all/emails-from-certain-senders-are-not-coming-through/00694bfd-a0ba-43b9-aba0-ec2d2d9a06f8

It looks like the recipient is refusing to accept mail from the outlook.com server - it could be due to something in the message or just outlook.com mail in general. Because it works with some mail - its either the subject/body text or if sage is adding the invoice as a pdf, the PDF attachement.

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Contact the recipient by some other means (by phone, for example) and ask them to tell their email admin that it appears that their email system is refusing connections from your email server.

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>>

1/12/2023 2:26:43 PM - Server at hotmal.com (20.103.85.33) returned '450 4.4.316 Connection refused [Message=Socket error code 10061] [LastAttemptedServerName=hotmal.com]

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