Exchange Contact Issue

Good day,

Over the weekend I pointed some of our other business's domains to our exchange server so that mail
can flow through it for security and functionality purposed.

Everything is working 100% except for 1 issue.

My ceo cannot send emails to one of the users.

I can send to that contact other users can send to that user but only he cannot as far as I am aware off. I presume it is a caching issue of some sorts or exchange is looking at a contact that may have been on the systel long ago as an Exchange contact.

The bounceback message that he receives has the following info. As one can see the To field has but at the start of this bounceback it is looking for something which does not exist as below :

How do i find this above entry and delete it off exchange? Or what should i do?

------------------------------------ Here the log starts-----------------------------------------------------------

Delivery has failed to these recipients or groups:

Ivan Da silva
The email address you entered couldn't be found. Please check the recipient's email address and try to resend the message. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:

Generating server: XXXXXXXXXXXX

Remote Server returned '550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found'

Original message headers:

 ( with Microsoft SMTP Server (TLS) id 15.0.847.32; Mon, 20 Jul
 2015 09:13:09 +0200
 15.00.0847.040; Mon, 20 Jul 2015 09:12:50 +0200
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Solomon Potgieter <>
To: Ivan Da silva <>
Subject: FW: BREAD Environment and Comfort
Thread-Topic: BREAD Environment and Comfort
Thread-Index: AdDCtYlSwQgVn7CWShGJpa9rB/4brAABekqQ
Date: Mon, 20 Jul 2015 09:12:50 +0200
Accept-Language: en-US, en-ZA
Content-Language: en-US
X-MS-Has-Attach: yes
MIME-Version: 1.0
X-Originating-IP: []
Leroy LuffHead of IT & DIgitalAsked:
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It seem that Outlook hold invalid cache contact. Please ask ceo to send a test email via OWA.

If it is working, rename the exisitin .ost file to .ost1, then re-create a new outlook profile. Before
Amit KumarCommented:
Check Contacts in Outlook if any exists with name, delete it and try to send e-mail
Simon Butler (Sembee)ConsultantCommented:
If it is just that one user who cannot send to that other user, then you need to look at their Outlook installation. Check for a Contact within their Contacts list that has the old address listed, also the nicknames file.

You can confirm it is an account issue by attempting to send to the same address from another account on your system. If that goes through correctly then it is purely that one user with the issue.

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Leroy LuffHead of IT & DIgitalAuthor Commented:
Hey Guys,

Sorry for Delay but here is an update :

I have looked at this issue and could not find a local contact on his outlook. Today this issue arrised on a 2nd users outlook.

So as far as I know all of us can email this user except 2 accounts. This means the problem can be on the exchange side aswell.

I think this is an issue to do with an external contact that existed for this user on Exchange previously and when deleted it did not properly delete. Is there shell commands i can use to check?

Or what do you guys suggest?
Simon Butler (Sembee)ConsultantCommented:
If everyone can email the recipient then it isn't a server side issue. If there was something left of the contact within the domain then it would affect everyone.

You have checked the auto complete list and ensured the entry is deleted from there?
If you check the address list on those two users, does the recipient exist? Does the problem happen in OWA?


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Leroy LuffHead of IT & DIgitalAuthor Commented:
Hi Guys,

So the issue is not resolved yet but these comments lead me to the problem. I will start a new thread for the problem.

It seems there is an issue with their GAL not updating. On their computers their GAL still reflects the contact as an external contact and not an internal contact. I know this as the icon of the contacts are different.

When trying to download OAB i get an error object not found.

Thanks to all that participated.
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