I have setup an Exchange 2010 server and moved my email account over to it, after a few weeks of testing I installed Outlook 2013 on my Windows 8 computer. Now when I send email to someone that is still on our old Exchange 2003 mail server it fails to deliver.
Delivery has failed to these recipients or groups:
recipient name
There's a problem with the recipient's mailbox. Please try resending this message. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: old.email.server
address I am sending to
#< #5.2.1> #SMTP#
Original message headers:
Received: from new.email.server ([172.16.2.17]) by old.email.server with
Microsoft SMTPSVC(6.0.3790.4675); Mon, 10 Dec 2012 11:48:02 -0600
Received: from new.email.server ([fe80::39aa:97e6:4aa0:e66a]) by
new.email.server ([fe80::39aa:97e6:4aa0:e66a%10]) with mapi id
14.01.0421.002; Mon, 10 Dec 2012 11:48:01 -0600
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Me <my.address>
To: Recipient <recipient.address>
Subject: test
Thread-Topic: test
Thread-Index: Ac3W/n4gLiECoPoTS6uhyoyOqYTQ6w==
Date: Mon, 10 Dec 2012 11:48:01 -0600
Message-ID: <*** Email address is removed for privacy ***>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator: *** Email address is removed for privacy ***
MIME-Version: 1.0
X-Originating-IP: [172.16.101.20]
Return-Path: my.address
X-OriginalArrivalTime: 10 Dec 2012 17:48:02.0368 (UTC) FILETIME=[8026DC00:01CDD6FE]
But if I reply to someone message it will go through with no problems.
I do have another user on the exchange 2010 server that is using Outlook 2010 and has no problems.
I can send from my phone and OWA with no problems.
So it seems like an Outlook 2013 problem.