Outlook Internal Address List Problem

I have taken a SBS2003 server, and used local move request to import all mailboxes into exchange 2010, then, used export-mailbox command to put them into a *.pst file.

Now, set up a new exchange server, and used import-mailbox to put them all back in.  

Now, using outlook, any e-mails John Smith sends me, come up John smith, no problem, but any emails John Smith sent me before the changeover, appear at the bottom of outlook as //FIRST ADMINISTRATIVE GROUP/JOHN SMITH and clicking "reply" says "could not find this recipient"  I have tried removing contact, editing contact, adding contact, etc.  I have also checked the GAL and it only shows the current contact on the current server.

Further.  If i go to send a NEW email to say Reception@server.com it gets there no problem, and reception can reply back to me.  HOWEVER, if reception emails me (a new email, not one from before the changeover), then if i click reply, it bounces back to me, and says "Reception@server.com - there is a problem with the users mailbox".  If i click reply, clear the recipient field, and manually type back in reception@server.com it resolves, and still bounces back saying error.  BUT if i go to create a NEW email, and type in reception@server.com, it resolves to the same address, same contact, but this time it sends no problem.

Have tried really hard to search through internal contacts, GAL, and client contacts to find any double ups or wrong settings but it seems so strange that the address letter for letter appears perfectly correct, and the exchange server mails me back with the exact address saying there is a problem with the mailbox.  Outside clients can email them back and forth no problem, and i can send new emails, but i cannot reply to them.  This is happening with most of our internal contacts, but even though i have erased them all at the outlook client, they still seem to resolve to the correct address, but the wrong location.

Thanks again.

Who is Participating?
MegaNuk3Connect With a Mentor Commented:
Basically you need to add X500 addresses to everyone's mailboxes for replying to old messages to work

The X500 will be the old Exchange 2003 legacyexchangedn of the mailbox. Did you do any AD exports?
Try deleting your NK2 file and see if that clears this up. I have a feeling that it will. You will need to do that for all users, but test it on yours first.

Let us know what happens.
Here is a little info on the NK2 file...


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Actually, let me suggest that you RENAME the NK2 instead, just in case it dissent work and you want it back... :)
ben_kapelAuthor Commented:
G'day there conradie,

I am happy to try this when I get back to the office, but let me just paint a bigger picture.. All of the computers are formatted fresh with windows 7 and the profiles have all been made
from nothing.  I would think the nk2 file was created when we did all this.

I am thinking perhaps and I could be wrong, that because references in the actual emails from before the changeover are wrong and point to the wrong location, that as soon as we open one and try reply to it, it adds an autocomplete entry to the wrong location.  

The *.pst files that were imported into these exchange mailboxes contained emails from our staff that reference back to our old exchange 2003 server.  I don't know how to rectify this

I have staff telling me "emails to tim and fred work, but to Jane and John, they don't.  When in all reality I know all the boxes work fine, but the emails in their inbox are creating old entries

thanks again for any help
The legacyexchangedn will look like
/o=org/OU=admin group/OU=recipients/CN=John smith

That needs to be added to the new John Smith mailbox as an X500 email address

How many mailboxes do you have?
ben_kapelAuthor Commented:
MegaNuk i think this is exactly it.  I remember in the old exchange everyone had a X.400 address...

So basically in outlook when we click on a message we received before having exchange 2010, and we click reply, this comes up:  The email address is no longer valid.

When i right click and goto outlook properties, this is displayed:


I can't update it or add it as a contact.

So... how do i do as you say, how to add these references to each persons mailbox ?  in EMC in the user mailbox properties ?

I did originally do a migration but there were far too many problems, therefore i used import-mailbox to get all the mailboxes into exchange 2010

Thanks again!

Yep copy that value and put in Gregs email addresses as an X500 address. You will probably have to say type is custom, then put type=X500 and then paste the legacyexchangedn value in

Then you should be able to reply to Gregs old mails
ben_kapelAuthor Commented:

That has helped bigtime for the contacts that came up with the wrong reference, however, some e-mails appear completely correct, yet they bounce back:

Delivery has failed to these recipients or groups:

John Fred (john@mycompany.net.au)
There's a problem with the recipient's mailbox. Please try resending the message. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:

Generating server: DC.mycompany.local

#550 5.2.0 STOREDRV.Deliver: The Microsoft Exchange Information Store service reported an error. The following information should help identify the cause of this error: "MapiExceptionInvalidEntryId:0.22318:3D000000, 4.19246:07010480, 0.28014:00000000, 4.24942:07010480". ##

Original message headers:

Received: from DC.mycompany.local ([]) by dc ([])
 with mapi; Thu, 18 Nov 2010 15:19:18 +0800
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Greg Smith <Greg@mycompany.net.au>
To: John Fred <john@mycompany.net.au>
Subject: RE: hi
Thread-Topic: hi
Thread-Index: AcuG8KM5DOIgTOJCQDC3cmzmnshXvwAADuww
Disposition-Notification-To: Greg Smith <Greg@mycompany.net.au>
Date: Thu, 18 Nov 2010 16:19:17 +0800
Message-ID: <491BB78C9241B446A9278027F12F6F9801381C25@dc>
References: <82AF340A089D06409984728B082AFA1B01360A1B@dc>
In-Reply-To: <82AF340A089D06409984728B082AFA1B01360A1B@dc>
Accept-Language: en-AU, en-US
Content-Language: en-US
X-MS-TNEF-Correlator: <491BB78C9241B446A9278027F12F6F9801381C25@dc>
MIME-Version: 1.0

The strange thing is if i click New Message, and type in Joh - It will correct to the full name "John Fred" and the email in brackets (john@mycompany.net.au), and it will send through fine.  But if i click REPLY on a message that John has sent me, it will STILL appear all correct, and right click look up contact the email address is perfectly fine, but i get the above rejection message.  Even if i clear the recipient field and re-type it in, it resolves fine and bounces back.

Once again, the mailboxes themselves all work fine, i have also tried deleting ALL contacts and autocompletes within outlook AND re-adding the contacts as well.  Nothing seems to be working.  Apart from the e-mail address is there other data within that that is corrupt/redundant ??



And you are using Outlook in MAPI (Outlook) mode? You aren't using pop3 or IMAP are you?
Is John Fred external to your company?
ben_kapelAuthor Commented:
Yep using outlook 2007 and 2010 in outlook exchange mode.  John Fred is internal

So no replies to old messages from internal people work? They all give the 5.2.0 STOREDRV.Deliver message?

When you repl to John Fred. Double click on his name in the TO box. Does it cone up as a mailbox with loads of tabs. I.e. Does it look the same as when you go into the GAL/Address Book and do properties on him?
ben_kapelAuthor Commented:
Actually, the old messages came up with the //first administrative group etc. Which we fixed by adding X500 tags to the addresses.  This is actually happening on new emails since the changeover,  when I look at the TO when replying it looks exactly the same as when I compose a new message (which works...)

So just to be sure, when you double click on the user's name in the "To" box you get all the tabs (General,Organization,Phone/Notes) on the user's name and it shows up as a mailbox instead of no tabs?
and john@mycompany.net.au is a valid email address on the "John Fred" mailbox?
MegaNuk3Connect With a Mentor Commented:
Hmmm, have you considered putting Exchange 2010 SP1 on there?

If that doesn't fix it then try these:
1.) create a new database and move John Fred to it. Can you reply to him now? If not move your mailbox to the new database, can you reply now?
2.) Please try:

1. download MFCmapi tool (http://mfcmapi.codeplex.com/releases/view/39272) onto the box where you have Outlook
2. create an Outlook profile against the mailbox that cannot receive mail (make it "online" rather than "cached" - to eliminate potential timing issue with  step 4)
3. Run MFC mapi, navidate to "Inbox" folder:
 Seesion -> Logon And Display Store Table
 Inbox is under Root, Top of the information store
4. Remove property 0x35EE0102 (I don't think it is named but if it is - then it is ptagAllItemsFolderEntryID)
(just to make sure - close and open MFCmapi and confirm that property is gone; chance of fatfinger is high - there are quite a few with the similar id)

Step 2 is from here where the same error is mentioned:

Step 1 will probably be easier to do against masses of mailboxes

That is if SP1 doesn't fix it
ben_kapelAuthor Commented:
Ok, I will try these things tomorrow.  Sounds promising.  Thank you.  In regards to SP1, is that as straightforward as running the setup or does it require a number of pre requisites?

SP1 is really straight forward. You should be able to just run the setup.

or do
setup.com /mode:upgrade
from the command prompt
ben_kapelAuthor Commented:

Thanks for your help.  Both of your solutions have solved my 2 problems.  Moving the mailbox into another database sorted out the invalid entryID fault.  I could not install SP1, but to be fair, i have opened another question for that:


Thanks for the update and the points
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