Exchange 2010 - Exchange Users Can Reply to Account But Cannot Send to It

I have a strange situation.  I had a user who setup loads of Outlook Rules, and corrupted his iPhone which was connected with ActiveSync.  The only way to get the iPhone to work again was to delete the entire Exchange email account, and start over.  That in turn has created another problem.  Users on the Exchange Server can reply to emails from the account, but cannot send emails from scratch.  They have tried using autocomplete, typing the email address in manually, and using the address book.  Here is an error message:

Delivery has failed to these recipients or groups:

Our Employee
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: EXCHANGE.dc1.contuso.com

IMCEAEX-_O=CONTUSO_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+28FYDIBOHF23SPDLT+29_CN=RECIPIENTS_CN=Our+20Employee02c@contuso.com
#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##

Original message headers:

Received: from EXCHANGE.dc1.contuso.com ([0.0.0.0]) by
 Exchange.dc1.contuso.com ([0.0.0.0]) with mapi id 14.01.0438.000; Fri,
 24 Jul 2015 12:46:58 -0700
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Our Employee2 our.employee2@contuso.com
To: Our Employee
        <IMCEAEX-_O=CONTUSO_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+28FYDIBOHF23SPDLT+29_CN=RECIPIENTS_CN=Our+20Employee02c@contuso.com>
Subject: testing2
Thread-Topic: testing2
Thread-Index: AdDGStCu6coxF6TUTLC2mS2k1xJvyw==
Date: Fri, 24 Jul 2015 12:46:56 -0700
Message-ID: <11E6675B7544C049B8B6FEC4ED0255E44BD51878@Exchange.dc1.contuso.com>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator: <11E6675B7544C049B8B6FEC4ED0255E44BD51878@Exchange.dc1.contuso.com>
MIME-Version: 1.0
X-Originating-IP: [0.0.0.0]
Also I am able to send emails to this account from outside the domain.  
Any assistance would be appreciated.
Michael


July 27th, 2015 3:34pm

You need to add legacyExchangeDN of old account as an x500 address of current mailbox.

/o=Contoso/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Our Employee

Look for the Method-2 in below KB just to Create an X500 proxy address for the old LegacyExchangeDN attribute for the user---- https://support.microsoft.com/en-us/kb/2807779

Free Windows Admin Tool Kit Click here and download it now
July 27th, 2015 6:55pm

Hi Michael,

Thank you for your question.

Did you try to send email from OWA to check if the issue persist?

If the issue just occur in outlook, we could rebuild the profile to check if the issue persist.

In addition, is there any modify in term of Received: from EXCHANGE.dc1.contuso.com ([0.0.0.0]) by Exchange.dc1.contuso.com ([0.0.0.0]) with mapi id 14.01.0438.000; Fri,, which my means is that if you change IP address?

You could refer to solution which Amit supply. If not, we could move mailbox to another database to check if the issue persist.

If there are any questions regarding this issue, please be free to let me know.

Best Regard,

Jim

July 28th, 2015 1:51am

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