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Exchange Internal Emails Bounce Back

I am having a strange problem. I have exchange 2013 with Domained joined clients and non domain clients. All running outlook 2007, 2010 or 2013

when I send an email from a joined domain client I can send internally and externally no problems.

however when I send from a non domain client I can send externally but not to internal clients. When I do I get the following error

Diagnostic information for administrators:

Generating server: 5RGS003.5rings.local

IMCEAEX-_o=5+20Rings+20IT_ou=First+20Administrative+20Group_cn=Recipients_cn=ashley+2Ehay-ellis@5rings.local
Remote Server returned '550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found'

Original message headers:
Received: from 5RGS003.5rings.local (172.16.0.15) by 5RGS003.5rings.local
(172.16.0.15) with Microsoft SMTP Server (TLS) id 15.0.620.29; Wed, 3 Jul
2013 09:47:55 +0100
Received: from 5RGS003.5rings.local ([192.133.70.102]) by 5RGS003.5rings.local
([::1]) with mapi id 15.00.0620.020; Wed, 3 Jul 2013 09:47:54 +0100
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Maxine Laker <Maxine.Laker@5ringstelecom.co.uk>
To: Ashley Hay-Ellis - 5 Rings IT
<IMCEAEX-_o=5+20Rings+20IT_ou=First+20Administrative+20Group_cn=Recipients_cn=ashley+2Ehay-ellis@5rings.local>
Subject: teste
Thread-Topic: teste
Thread-Index: Ac53ygAOl1o1RA6BQGiTdtLe4wltkQ==
Date: Wed, 3 Jul 2013 09:47:53 +0100
Message-ID: <24cbf6b76dda451bafa70b7d2767881f@5RGS003.5rings.local>
Accept-Language: en-GB, en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator: <24cbf6b76dda451bafa70b7d2767881f@5RGS003.5rings.local>
MIME-Version: 1.0
X-Originating-IP: [164.40.217.14]
Return-Path: Maxine.Laker@5ringstelecom.co.uk

This is very strange and cant see an obvious reason for the problem.

Other points that might be needed, I have a signed and authorised SSL certificate not an self signed one. The problem occurs on XP, Server 2003 and windows 7 and 8 machines.

Kind Regards
Ashley

Kind Regards
Ashley

the_endjinn

I'm pretty sure that means your internal (non-domain) users have legacy email addresses that can't be resolved. The error means the recipient is not found, do the non-domain users not have SMTP email addresses?

This can also be caused by the offline address book or Outlook nickname cache (.nk2 file in your Outlook profile). Try clearing these on one of the clients that can't send to internal addresses and then try again.

purpleoak

ASKER

this issue occurs on any internal address we try to send to.

for instance user Peter has a workstation on domain and he can email Daniel on domains no problems.

however if peter sends from his laptop not on domain to Daniel on domain he gets an error.

so the addresses are all setup correctly. I have tried to type the address in full, and select the address from the To box incase it was the NK2 import that broke it.

Kind Regards
Ashley

ASKER CERTIFIED SOLUTION

Simon Butler (Sembee)

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purpleoak

ASKER

It worked, it was the NK2 file that we took from the old domain profiles. So It was the X500 address its trying to email. I have removed from the NK2 files and then added the new ones via the "alt K" button.

Thanks for all your help.