Link to home
Start Free TrialLog in
Avatar of brightergreen
brightergreen

asked on

Cached internal addresses not delivering after exchange migration

When migrating clients to new exchange servers (with a new internal domain) we often have the problem that users get NDRs when responding or sending new (via NK2 / Outlook 2010 cache) messages to users. Here is an example of the bounceback (personal data changed).

IMCEAEX-_O=THE+RED+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=BOB@thered.com
#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##

To fix this, we've gone in and deleted individual entries from PSTs or entire PSTs, but at this point we're working with an organization that frequently needs to respond to old emails. I feel there must be a fix for this we can perform on the server for the whole organization.

Clients range from outlook 2003 - 2010
Server was exchange 2003 and now is SBS 2011

Here is the header from that mail:

Received: from TRSBS1.tr.local ([fe80::34fb:c8ef:91c3:a07c]) by
 TRSBS1.tr.local ([fe80::34ab:c2ef:94c3:g07c%11]) with mapi id
 14.01.0218.012; Fri, 29 Jul 2011 20:48:11 -0700
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: jon <jon@thered.com>
To: "'bob@Thered.com'"
        <IMCEAEX-_O=THE+20RED+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=bob@Thered.com>
Subject: FW: red
Thread-Topic: red
Thread-Index: AcxOSo9kxFPrLujoTo+/YMgMbjSJ8QAIObLQ
Date: Fri, 29 Jul 2011 20:48:10 -0700
Message-ID: <472B6462B6A36746BDBBFA1DBE47F7BFD7A1B0@TRSBS01.tr.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator: <472B6462B6A36746BDBBFA1DBE47F7BFD7A1B0@TRSBS01.tr.local>
MIME-Version: 1.0
X-Originating-IP: [10.10.4.136]
ASKER CERTIFIED SOLUTION
Avatar of Alan Hardisty
Alan Hardisty
Flag of United Kingdom of Great Britain and Northern Ireland image

Link to home
membership
This solution is only available to members.
To access this solution, you must be a member of Experts Exchange.
Start Free Trial
Avatar of brightergreen
brightergreen

ASKER

Tried alanhardisty's proposed solution on the technet blogs - for future users, please test this carefully when applying this to SBS 2011, in our case it corrupted our email addresses on the AD objects and caused all the objects it was applied to to lose all their email addresses. Fortunately we had made a backup of AD and were able to restore.

However, the theory seems sound - we got the x500 addresses in there but they are still not working. I've tried many versions of the syntax for the x500 address including:

_O=THE+20RED+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=bob@Thered.com

O=THE+20RED+20ORGANIZATION_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=bob@Thered.com

“_O=THE RED ORGANIZATION_OU=FIRST ADMINISTRATIVE GROUP_CN=RECIPIENTS_CN=bob@Thered.com”

“O=THE RED ORGANIZATION_OU=FIRST ADMINISTRATIVE GROUP_CN=RECIPIENTS_CN=bob@Thered.com”

/O=THE+20RED+20ORGANIZATION/OU=FIRST+20ADMINISTRATIVE+20GROUP/CN=RECIPIENTS/CN=bob@Thered.com

O=THE+20RED+20ORGANIZATION/OU=FIRST+20ADMINISTRATIVE+20GROUP/CN=RECIPIENTS/CN=bob@Thered.com

I fired up the old exchange server and had a look at the LegacyExchangeDN attribute and this is what it was for that user, which differs from the original bounceback (and also did not work):

o=The Red Organization/ou=First Administrative Group/cn=Recipients/cn=bob

What is the correct syntax for the x500 address? Is there another component I'm missing?
Got it.

The X500 has to be the old LegacyExchangeDN in this format (my final syntax as missing a front slash):

/o=The Red Organization/ou=First Administrative Group/cn=Recipients/cn=bob

which appears to correspond with the mailbox name, not an SMTP address.
I've requested that this question be closed as follows:

Accepted answer: 0 points for brightergreen's comment http:/Q_27249508.html#36410226

for the following reason:

Ended up being a syntax error that I was able to resolve myself.
So I didn't help you at all with the solution by advising you about the x500 address?