Undeliverable emails to recreated exchange profiles


I encountered a problem with a set of emails on exchange. Currently some users whom try to send out a mail to the internal emails they receive a undeliverable email message upon sending the mail. The full message is as follows:

From: Microsoft Outlook
Sent: Friday, January 09, 2015 8:22 AM
To: Adalberto Rodriguez
Subject: Undeliverable: FW: Account #601862 FleetOne Reports

Delivery has failed to these recipients or groups:
Ivan Canchola
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.
Marisela Fonseca
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: UP-MS1.uptrucking.local
#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##
#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##
Original message headers:
Received: from UP-MS1.uptrucking.local ([fe80::95a2:a66e:596:7bd6]) by
 UP-MS1.uptrucking.local ([fe80::95a2:a66e:596:7bd6%13]) with mapi id
 14.01.0438.000; Fri, 9 Jan 2015 08:21:42 -0600
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Adalberto Rodriguez <arodriguez@uptrucking.com>
To: "p.gutierrez@borderfreight.com" <p.gutierrez@borderfreight.com>,
        "Ulisesgro@borderfreight.com" <Ulisesgro@borderfreight.com>, Everado Gonzalez
        <egonzalez@uptrucking.com>, Osvaldo Puente <opuente@uptrucking.com>, Higinio
 Tijerina <htijerina@uptrucking.com>, "Ivan  Canchola"
        Marisela Fonseca
Subject: FW: Account #601862 FleetOne Reports
Thread-Topic: Account #601862 FleetOne Reports
Thread-Index: AQHQK91P4aMsiN+uVU2WKzsnyrTndpy3121w
Sensitivity: company-confidential
Date: Fri, 9 Jan 2015 08:21:41 -0600
Message-ID: <CBACBD78DCE17E4D82705C16E595168C1B10B959@UP-MS1.uptrucking.local>
References: <201501090724.t097NmQ0020874@nas2-mail1.fleetone.com>
In-Reply-To: <201501090724.t097NmQ0020874@nas2-mail1.fleetone.com>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator: <CBACBD78DCE17E4D82705C16E595168C1B10B959@UP-MS1.uptrucking.local>
MIME-Version: 1.0
X-Originating-IP: []

Initially the two users listed in the message are on the same domain and are also able to send and receive emails are able to work with no other issues on the network.  

Previously what was done to the users that the message was unable to deliver, their profiles were recreated to a previous issue with a program that was not working. The profiles were removed locally on the computers as well recreated on the server.

Another mention is that there are two exchange databases on the server , but only one is mounted in exchange and the other is only needed when new users are created , their exchange profiles have to be requested to move onto the new database.

So far what only seems to work by a day by day basis, is to remove the auto-complete instance of the email/contact and manually email it. This only seems to work only day by day, requiring me to do the same method every time.

User computers are running Win 7 Pro, with Office 2013.
Small Business Server 2011 with Exchange 2010
Who is Participating?
BahloulConnect With a Mentor Commented:

- make sure the sender  select the recipient from GAL not from the recent drop list.

- anti-spam or antivirus software that might be intercepting the message for some reason and deleting or quarantining it? If so, check the log/archive files for that software and see if the messages are present

- use message tracking might help.

- Make sure the recipient mailbox can receive messages from all sender which include internal / external clients

in the EAC, navigate to Recipients > Mailboxes click the mailbox that you want to check  message delivery restrictions for, Edit icon on the mailbox properties page, click Mailbox Features / Under Message Delivery Restrictions, click View details to view and change the following delivery restrictions:
Accept messages from  Make sure that All sender is selected.

DaveConnect With a Mentor Commented:
As the users MAPI profile is part of their roaming profile, is it saving properly when the user logs off. It might be worth renaming the server copy of the profile to make sure it updates.

This problem can also be cured by adding an X.500 entry for the bad address to the failing users. The instructions are here:-


which says:-

The legacyExchangeDN attribute is stored in the user's auto-complete file. If this attribute is changed for any reason, contacts that send email message to the user will have the email returned together with a 5.1.1 NDR. Although the steps that are provided in this article resolve the issue, this procedure has to be performed by each user individually. To avoid this ongoing problem, an x500 address can be added to the user's EmailAddresses (proxyAddresses) attribute. To do this, follow these steps:
1.Review the NDR to analyze the address to which the users are trying to send email messages. The address will be similar in format to the following:

Note This format indicates that the legacyExchangeDN attribute is translated by Exchange to an SMTP address.  

2.Translate the address to legacyExchangeDN format. To do this, follow these steps:
           a. Remove IMCEAEX-.
           b. Replace any underscore (_) with a forward slash (/).
           c. Replace +20 with a blank space.
           d. Replace +28 with an opening parenthesis.
           e. Replace +29 with a  closing parenthesis.
For example, the address in step 1 would become the following:


3.Review the user's legacyExchangeDN attribute. If it does not match the legacyExchangeDN attribute that is in the user's auto-complete file, add  legacyExchangeDN as an x500 address on the user's object by using the Active Directory Service Interfaces (ADSI) Edit tool or the Ldp GUI tool. Do not change the legacyExchangeDN attribute unless you are directed to do this by Office 365 Support.
ctagleAuthor Commented:
everything is resolved, thank you for the help.
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