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Email bouncing before it even leaves the SBS2011 server

Posted on 2013-05-22
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Last Modified: 2013-05-22
We are using exchange on SBS2011 and the POP connector to access mailboxes on a 1and1.com hosted site.

After completing a recent SBS2003 to SBS2011 migration, one of the forwarding email accounts on the 1and1.com site is not working.

Specifically, there is a forwarding account setup on 1and1.com, where email sent to:

staff@mycompany.com

gets forwarded to:

person1@mycompany.com
person2.@mycompany.com
person3@mycompany.com

It still works when I send a message to staff@mycompany.com from any other mail system, such as from my comcast account.

While logged on to a computer in the office where the SBS2011 server resides, as soon as I send a message via Outlook, I get an immediate reply:

Delivery has failed to these recipients or groups:

staff@mycompany.com (staff@mycompany.com)
The e-mail address you entered couldn't be found. Please check the recipient's e-mail address and try to resend the message. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:

Generating server: SERVER2.mycompany.local

staff@mycompany.com
#550 5.1.1 RESOLVER.ADR.RecipNotFound; not found ##

Original message headers:

Received: from SERVER2.mycompany.local ([fe80::38cc:60ab:9271:3737]) by
SERVER2.mycompany.local ([fe80::38cc:60ab:9271:3737%12]) with mapi id
 14.01.0218.012; Wed, 22 May 2013 17:23:02 -0500
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Julie Smith <Julie@mycompany.com>
To: "staff@mycompany.com" <staff@mycompany.com>
Subject: test #1 5:22PM
Thread-Topic: test #1 5:22PM
Thread-Index: Ac5XOumg7LBUvt/yTGOIfsoeHipMOw==
Date: Wed, 22 May 2013 17:23:01 -0500
Message-ID: <2D7FC9CE8203574BBB7B6CA9815044CB02325D@SERVER2.mycompany.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator: <2D7FC9CE8203574BBB7B6CA9815044CB02325D@HA-SERVER2.hm.local>
MIME-Version: 1.0
X-Originating-IP: [192.168.1.65]

Why is the local exchange server intercepting this email message? I expect it to go out through the SMTP server and then back in through the POP connector.
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Question by:itplatoon
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2 Comments
 
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Accepted Solution

by:
Simon Butler (Sembee) earned 2000 total points
ID: 39189414
That isn't how Exchange works.
You must have the domain in the list of accepted domains. Exchange then presumes it is responsible for all email for the domain. It will not send it straight out.

The POP3 connector isn't really designed for long term use, it is designed to help you move to Exchange and use SMTP delivery.

Simon.
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Author Closing Comment

by:itplatoon
ID: 39189469
Yes, that makes sense now that you call that out. For the short run, I created a distribution group with the same name and it works as expected now.
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