Pfsense Office 365 Smtp
When sending ane-mail from O365 migrated users to On-premise users the On-premise users don't get e-mails.
I created an STMP relay for our Office 365 instance, following option #3 in this document: How to set up a multifunction device or application to send email using Microsoft 365 or Office 365. The instructions include a suggested change to the DSN records. In this scenario I would like to allow SMTP traffic to my internet provider so that an application in my test environment is able to send notification messages. In this environment I use pfSense. For this to work, you have to create a port forwarding rule on the LAN interface forwarding traffic to any IP with port 587.
Failure Message
Pfsense Office 365 Smtp Configuration
Pfsense Office 365 Smtp Settings
From: Microsoft Outlook <MicrosoftExchange329e71ec88ae4615bbc36ab6ce41109e@domain.onmicrosoft.com> May 07, 2018 Click here to get the best price Chrysler Navigation Updates on Disc and everything you need to know in order to keep the Chrysler GPS up to date with new maps.Jeep & Dodge REC/RB1 navigation disc version AI.2018 hot new men/women nmd#1 eqt#1 running sports shoes. Chrysler navigation rb1, rec radio dvd update disc torrent cheering up quotes after a bad day.' / na Blog.cz Rb1, rec radio dvd update March 19, 2016, 12:36 映画や音楽、本などに関する情報を集めた「naverまとめ」のエンタメ情報チャンネルです。. This genuine Mopar DVD disc is for 2004-2007 CHRYSLER & JEEP owners who have a REC, or RB1 navigational radio can now update their radio with this newly released dvd disc from Chrysler. It contains 6.1 million miles of roads, points of interset such as restaurants, hotels, and gas stations. Delivery has failed to these recipients or groups: User (User@domain.com.tr) Please try sending this message again. If the problem continues, contact your helpdesk. User2 ( Company ) (User2@domain.com.tr) Please try sending this message again. If the problem continues, contact your helpdesk. Diagnostic information for administrators: Generating server: DB4PR03MB532.eurprd03.prod.outlook.com User (User@domain.com.tr)
User2 ( Company ) (User2@domain.com.tr) 4/4/2014 7:27:34 PM - Remote Server at emea01-internal.map.protection.outlook.com (10.47.216.25) returned '450 4.7.0 Proxy session setup failed on Frontend with '451 4.4.0 Primary target IP address responded with: '451 5.7.3 STARTTLS is required to send mail.' Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts. The last endpoint attempted was 210.179.31.5:25' Original message headers: Received: from DB4PR03MB610.eurprd03.prod.outlook.com (10.141.234.156) by DB4PR03MB532.eurprd03.prod.outlook.com (10.141.235.143) with Microsoft SMTP Server (TLS) id 15.0.908.10; Wed, 2 Apr 2014 19:31:29 +0000 Received: from DB4PR03MB610.eurprd03.prod.outlook.com (10.141.233.156) by DB4PR03MB610.eurprd03.prod.outlook.com (10.141.234.156) with Microsoft SMTP Server (TLS) id 15.0.898.11; Wed, 2 Apr 2014 12:49:18 +0000 Received: from DB4PR03MB610.eurprd03.prod.outlook.com ([10.141.233.156]) by DB4PR03MB620.eurprd03.prod.outlook.com ([10.141.233.156]) with mapi id 15.00.0913.002; Wed, 2 Apr 2014 12:49:17 +0000 Content-Type: multipart/mixed; boundary='_000_2c4cf07ee43e4faab98dc52f068a566fDB4PR03MB620eurprd03pro_' From: test <test@domain.com.tr> To: 'User ( Company )' <user@domain.com.tr>, 'User2 ( Company )' <User2@domain.com.tr> Subject: deneme Thread-Topic: deneme Thread-Index: Ac9Oce26frtuRTMySYWFyAvAom/lyQ Date: Wed, 2 Apr 2014 12:49:16 +0000 Message-ID: <2c4cf07ee43e4faab98dc52f068a566f@DB4PR03MB620.eurprd03.prod.outlook.com> Accept-Language: en-US Content-Language: en-US X-MS-Has-Attach: X-MS-TNEF-Correlator: <2c4cf07ee43e4faab98dc52f068a566f@DB4PR03MB620.eurprd03.prod.outlook.com> x-originating-ip: [78.186.201.28] X-Forefront-Antispam-Report: SFV:SKI;SFS:;DIR:INB;SFP:;SCL:-1;SRVR:DB4PR03MB610;H:DB4PR03MB620.eurprd03.prod.outlook.com;FPR:;LANG:tr;;SKIP:2; MIME-Version: 1.0 X-MS-Exchange-CrossPremises-AuthAs: Internal X-MS-Exchange-CrossPremises-AuthMechanism: 03 X-MS-Exchange-CrossPremises-AuthSource: DB4PR03MB620.eurprd03.prod.outlook.com X-MS-Exchange-CrossPremises-SCL: -1 X-MS-Exchange-CrossPremises-messagesource: StoreDriver X-MS-Exchange-CrossPremises-BCC: X-MS-Exchange-CrossPremises-originalclientipaddress: 78.186.201.28 X-MS-Exchange-CrossPremises-avstamp-service: 1.0 X-MS-Exchange-CrossPremises-antispam-scancontext: DIR:Originating;SFV:SKI;SKIP:0; X-MS-Exchange-CrossPremises-processed-by-journaling: Journal Agent X-MS-Exchange-CrossPremises-ContentConversionOptions: True;00160000;True;; X-OrganizationHeadersPreserved: DB4PR03MB610.eurprd03.prod.outlook.com Return-Path: test@domain.com.tr X-OriginatorOrg: domain.com.tr Symptoms When you try to telnet the Office 365 hub transport from Exchange on-premises server it won't recognize the telnet commands on the SMTP server. Resolution: 451 4.4.0 Primary target IP address responded with: '451 5.7.3 Must issue a STARTTLS commnd first' Office 365 Hybrid
The errors suggest the TLS connection cannot be made but a TLS certificate IS present and during the Hybrid Connection Wizard the required connectors are automatically created so should not require an additional configuration.
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