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New to the email hosting scene - running an Exchange 2013 box.

Email is always (literally, always) marked as spam when sending out to my outlook.com account. Whereas if its sent to an email address hosted by Office365, it goes through fine.

IP isnt on any block lists or anything like that and SPF records are all intact apparently (v=spf1 ip4:212.xxx.108.199 ip4:192.168.1.150 -all (where .150 is the internal IP of the exchange box)

RDNS is rdns.technicaldomain.co.uk and resolves to my public IP - 212.xxx.108.199. The email address I'm trying to send email from is testinguser@technicaldomain.co.uk

Header is as follows (i've removed my email, part of the public IP and changed the domain to 'technicaldomain.co.uk')

Might be useful to point out that 'technicaldomain.co.uk' is the domain used for Active Directory (again, its not 'technicaldomain.co.uk' but something similar - just dont want to post it up on the internet for obvious reasons). The exchange server is at exchangeserver.technicaldomain.co.uk. 

    x-store-info:4r51+eLowCe79NzwdU2kR3P+ctWZsO+J
Authentication-Results: hotmail.com; spf=pass (sender IP is 212.xxx.108.199) smtp.mailfrom=testinguser@technicaldomain.co.uk; dkim=none header.d=technicaldomain.co.uk; x-hmca=pass header.id=testinguser@technicaldomain.co.uk
X-SID-PRA: testinguser@technicaldomain.co.uk
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02
X-Message-Info: [removed]
Received: from exchangeserver.technicaldomain.co.uk ([212.xxx.108.199]) by COL004-MC2F35.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23008);
     Sat, 27 Jun 2015 14:45:22 -0700
Received: from exchangeserver.technicaldomain.co.uk (192.168.1.150) by
 exchangeserver.technicaldomain.co.uk (192.168.1.150) with Microsoft SMTP
 Server (TLS) id 15.0.847.32; Sat, 27 Jun 2015 22:44:32 +0100
Received: from exchangeserver.technicaldomain.co.uk
 ([fe80::11ce:106e:d30f:b46e]) by exchangeserver.technicaldomain.co.uk
 ([fe80::11ce:106e:d30f:b46e%12]) with mapi id 15.00.0847.030; Sat, 27 Jun
 2015 22:43:55 +0100
From: Technical Gateway <testinguser@technicaldomain.co.uk>
To: "my.email@outlook.com" <my.email@outlook.com>
Subject: Testing
Thread-Topic: Testing
Thread-Index: AQHQsSJdqKa07/ELK0+2pr2mZbC2DA==
Date: Sat, 27 Jun 2015 21:43:55 +0000
Message-ID: <dd927b4a51024fb08c8680a74ca2f2fb@exchangeserver.technicaldomain.co.uk>
Accept-Language: en-GB, en-US
Content-Language: en-GB
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
x-originating-ip: [192.168.1.100]
Content-Type: multipart/alternative;
    boundary="_000_dd927b4a51024fb08c8680a74ca2f2fbexchangeservertechnical_"
MIME-Version: 1.0
Return-Path: testinguser@technicaldomain.co.uk
X-OriginalArrivalTime: 27 Jun 2015 21:45:22.0767 (UTC) FILETIME=[91D90DF0:01D0B122]
FoolishlyWise
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    Your rdns and outbound server name should be the same. So if the server sends exchangeserver.technicaldomain then exchangesever.technicaldomain should resolve to the same ip. – Drifter104 Jun 27 '15 at 22:26
  • exchangeserver.technicaldomain.co.uk does resolve to the public IP correctly (212.xxx.108.199). – FoolishlyWise Jun 27 '15 at 22:30
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    But the reverse DNS for the .199 address should return exchangeserver.technicaldomain not rdns.technicaldomain – TessellatingHeckler Jun 28 '15 at 03:05
  • That's now been raised with the ISP for change. Out of interest, if I decide to use another domain for email (eg: datadomain.co.uk) BUT leave the rdns and Active Directory Domain as technicaldomain.co.uk, would this cause issues? Or would I need to change the rdns and Active Directory stuff to exchangeserver.datadomain.co.uk? – FoolishlyWise Jun 28 '15 at 11:53

0 Answers0