Problems sending mails to hotmail.com and live.com adresses from Office365

We have faced the same issue, with a Friendly From Name including a "ë", every single email were bouncing to Microsoft.

Replacing the "ë" by "e" fixed the situation.

Thanks for the tip

Bom dia,

Estou com o mesmo problema.

Se alguem tiver alguma solução favo informar.

Servidores da microsoft informar que receberem o email, porem apos alguns minutos retorna com email informando:

Delivery has failed to these recipients or groups: F & S COMERCIAL LTDA (@outlook.com) The email system had a problem processing this message. It won't try to deliver this message again. Diagnostic information for administrators: Generating server: MN2PR02MB6829.namprd02.prod.outlook.com @outlook.com Remote server returned '550 5.6.0 CAT.InvalidContent.Exception: DataSourceOperationException, proxyAddress: prefix not supported - ; cannot handle content of message with InternalId 141875654694777, InternetMessageId <@AM6EUR05FT066.eop-eur05.prod.protection.outlook.com>.' Original message headers: Received: from AM6PR08CA0013.eurprd08.prod.outlook.com (2603:10a6:20b:b2::25) by MN2PR02MB6829.namprd02.prod.outlook.com (2603:10b6:208:199::13) with Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6340.21; Wed, 26 Apr 2023 12:10:16 +0000Received: from AM6EUR05FT066.eop-eur05.prod.protection.outlook.com (2603:10a6:20b:b2:cafe::96) by AM6PR08CA0013.outlook.office365.com (2603:10a6:20b:b2::25) with Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6340.21 via Frontend Transport; Wed, 26 Apr 2023 12:10:16 +0000Authentication-Results: spf=pass (sender IP is 177.159.117.107) smtp.mailfrom=apti.com.br; dkim=pass (signature was verified) header.d=apti.com.br;dmarc=none action="none" header.from=;Received-SPF: Pass (protection.outlook.com: domain of apti.com.br designates 177.159.117.107 as permitted sender) receiver=protection.outlook.com; client-ip=177.159.117.107; helo=reverso.apti.com.br; pr=CReceived: from reverso.apti.com.br (177.159.117.107) by AM6EUR05FT066.mail.protection.outlook.com (10.233.240.108) with Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.6340.21 via Frontend Transport; Wed, 26 Apr 2023 12:10:14 +0000X-IncomingTopHeaderMarker: OriginalChecksum:0AFA6E298765BC569708138C93B1EACD77B00EDE25215930BF4D1EAE15ACC0CA;UpperCasedChecksum:C0DEBB3C5BF62167B2A69E0264DCCE2EC965C8A0FBF63C17F54751E6F40F264F;SizeAsReceived:1627;Count:16Comment: DKIM? See http://www.dkim.orgDKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=apti.com.br; s=default; x=1683115814; h=Comment: DomainKey-Signature:Received:S4-id:Mail-From:Received:From:To: Subject:MIME-Version:Content-Type:Content-Transfer-Encoding; bh=vOOnhtpycwoMEvTETuBJ5FmtsjKgkjWfGY6sajDCN00=; b=LsZtbWQpqg+JN ZYjwkZSDy9W89b1yGVmubUkjLIwk8w8rQryfiKBjuyjuDyRnLmFKxs39eqNqPsVM r00P+XJ1QMd2h0FZ2XHHZRUgBLN6LZ15QmHGwG1qQ8yWP2IhMxmgp+FORfJ7kT9I yMUxbhKObqySS06YzyYNC32gzsvwec=Comment: DomainKeys? See http://antispam.yahoo.com/domainkeysDomainKey-Signature: a=rsa-sha1; q=dns; c=nofws; s=default; d=apti.com.br; h=Received:S4-id:Mail-From:Received:From:To:Subject:MIME-Version:Content-Type:Content-Transfer-Encoding:X-Antivirus:X-Antivirus-Status; b=BHDBPyJthvD0aqxUWpqqi2z06QPI1NSqRnAElMBLYBZ8AjxtDxWeRrpBqj0LOE IX/9GzKQdUoIBqX4bzNlICORFlrkaEqvvt9U6X5Ryqib08yk2GUPZzAvyDWkoWvX lf4DVT4l1574lIUUER+cnZSkgdInL6kQs4V8RxZY3s4Ks=;Received: (qmail 37410 invoked by uid 89); 26 Apr 2023 09:10:11 -0300S4-id: mail1682511009371941009kxfaq.emlMail-From: @apti.com.brReceived: from unknown (HELO localhost) (@apti.com.br) by apti.com.br with ESMTPA; 26 Apr 2023 09:10:09 -0300From: @apti.com.br To: F & S COMERCIAL LTDA Subject: Apti Alimentos Ltda. - Recebemos seu Pedido Nº 5852MIME-Version: 1.0Content-Type: multipart/related; boundary=2eece4376cee1433d0e9f200deb75408Content-Transfer-Encoding: 8bitX-Antivirus: Avast (VPS 230426-2, 26/4/2023), Outbound messageX-Antivirus-Status: CleanX-IncomingHeaderCount: 16Message-ID: <@AM6EUR05FT066.eop-eur05.prod.protection.outlook.com>Return-Path: @apti.com.brDate: Wed, 26 Apr 2023 12:10:14 +0000X-EOPAttributedMessage: 0X-EOPTenantAttributedMessage: 84df9e7f-e9f6-40af-b435-aaaaaaaaaaaa:0X-MS-PublicTrafficType: EmailX-MS-TrafficTypeDiagnostic: AM6EUR05FT066:EE_|MN2PR02MB6829:EE_X-MS-UserLastLogonTime: 4/26/2023 12:09:28 PMX-MS-Office365-Filtering-Correlation-Id: 92b5b177-281c-4796-3291-08db464f318c Reporting-MTA: dns;MN2PR02MB6829.namprd02.prod.outlook.com Received-From-MTA: dns;reverso.apti.com.br Arrival-Date: Wed, 26 Apr 2023 12:10:16 +0000 Final-Recipient: rfc822;@outlook.com Action: failed Status: 5.6.0 Diagnostic-Code: smtp;550 5.6.0 CAT.InvalidContent.Exception: DataSourceOperationException, proxyAddress: prefix not supported - ; cannot handle content of message with InternalId 141875654694777, InternetMessageId <@AM6EUR05FT066.eop-eur05.prod.protection.outlook.com>. X-Display-Name: F & S COMERCIAL LTDA

Nao consigo contato com o suporte microsoft no Brasil.

No aguardo

Dayan

We have had the same issue for a couple for a couple of weeks - we use exchange online to ensure deliverability to Microsoft domains as we found MS tends to junk many emails.

Our site's IP is listed in the connector under the Exchange Admin and until very recently was working fine but now we are getting 550 Undeliverable reports for any emails that are Microsoft domains (eg hotmail, live, outlook) being sent via PHP on our server. Sending emails from Outlook or Mac Mail still get delivered as expected, its just our web server thats failing.

I am on a ticket with MS support but they are trying to convince me that the problem is at the recipients side - this doesn't fill me with confidence being as Microsoft are the recipients.

I wondered whether the few patches mentioned by the answer need to be rolled out to their own servers for Exchange Online?

Hi' Peter

Yes, :-)

Regards

Jakob Heldorf