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New Exchange 2010 server, users on old Exchange 2003 servers cannot email to users that were on the old server, now on the new.

Posted on 2010-11-15
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Last Modified: 2012-05-10
I have an Exchange 2003 server, configured with a .local domain name.  There are a number of organizations and domains on this server.  

I created a new Exchange 2010 server, on a new external IP.  This server's domain is the .com equivalent of the .local domain from the 2003 server.  

I deleted some accounts from the 2003 server.  I removed the domains from the recipient policies on the 2003 server.  

The new server (2010) is working nicely, sends/receives email no problem.  

The issue is that users on the OLD server, who try to email users who are now on the NEW server, get NDR's.  It seems the 2003 server is "remembering" that these were once locally connected accounts, but now are "external" addresses.

Basically, users on the old server can't email users on the new server, IF they existing on the old server previously.  Everything else is fine...

Tips appreciated.
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Question by:mikeshaver
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by:Radhakrishnan Rajayyan
ID: 34142840
You have to create an MX record from your dns then only both servers can able to communicate (exchange mails) each other.
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by:mikeshaver
ID: 34142850
Huh?  In the DNS settings on the old server, add an MX record for the domain of the new server?  My MX is working externally...its handled by GoDaddy.

I'm not sure what you are suggesting?
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by:Radhakrishnan Rajayyan
ID: 34142906
Is these 2 servers are in the same network or different network? Have you enabled trust relationship between these 2 domain?
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by:mikeshaver
ID: 34142926
Totally different servers, on different networks.  There is no relationship between them, nor do I want their to be.

Here's a better explanation of what I have done:

user@domain.com was on server 2003.  I deleted this account, removed the recipient policies for accepting mail to "domain.com"  The MX record for domain.com has been changed from the IP of the 2003 server, to the IP of the 2010 server.  Anyone external can email user@domain.com on the NEW server.

The issue is when a user who is still on the 2003 server, say user@differentdomain.com, tries to email user@domain.com.  That mail gets rejected.  It only happens if the originating user is on the OLD server, trying to send to someone who WAS on the old server, but is now on the NEW server.

Mike
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by:Radhakrishnan Rajayyan
ID: 34143042
Is the old server has static public IP configured for send & receive mails for outside the world, I guess that , as per your explanation you have removed the recipient policy and public ip from the old server, So it dosent have any access to the external world now, So obviously whatever the mail you are trying to send out side of your office it will bounce back, At the same time you can communicate internally if SMTP/POP services configured.
Please have a look at these articles for more information.
http://technet.microsoft.com/en-us/library/aa996314.aspx
http://serverfault.com/questions/108815/setting-up-two-exchange-servers-to-receive-mail-on-their-old-domains-while-sendin
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by:mikeshaver
ID: 34143094
No, the old server still has its same public IP.  There are still other domains (other than the one I relocated to the new server) on the server, which is running fine still.

The new server has a NEW public IP and is completely separate from the old server.  

Some email addresses (which work from external) on the NEW server were previously on the old server.   If anyone on the OLD server tries to mail someone that WAS on the old server, but is now on the new server....rejection.  It only occurs when someone on the OLD server tries to email someone on the NEW server that WAS on the old server.
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by:Radhakrishnan Rajayyan
ID: 34143138
Ok...So you have deleted some user accounts from the old server, After that what happens in exchange environment it will not delete immediately (mailbox), Have you deleted their mail boxes too? if not,  Go to exchange system manager from the old server and select the deleted users mail box and account and purge it, so it will delete permanently.
Check once whether it will resolve the issue.
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Radhakrishnan Rajayyan earned 167 total points
ID: 34143285
Also you have to check these setting .The name of the SMTP virtual server (Exch sys mgr / Admin groups / Site / Servers / email server / protocols / smtp  ... properties of server / Delivery Tab / Advanced button )  (or Exchange System Manager, Server, Expand your server, Protocols, SMTP,Default smtp virtual server, Properties, Delivery,Advanced button ) is an internal (to the company) dns name which must be different from the email server's external dns name.  You have to give a dns entry for it's external dns name.   So you needed to add a dns entry on the internet for it's internal name also.
Or maybe the same entry you are using for your new server.
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by:markusdamenous
ID: 34145080
Hi

You need to remove the email address entries for the user who has moved, on the Outlook client of the user on the old system.

What will be happening is that Exchange when it communicates, doesnt use SMTP address.  It uses internal addressing.  The Outlook NK2 or autosuggest cache contains the internal addressing.

You can delete these entries, by highlighting them and pressing Delete
OR
NK2 edit, a small program that is free to download that can remove entries from the NK2 file.  Remove all the entries of type EX.
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by:mikeshaver
ID: 34145951
Hi Mark

The error is occurnig from web access as well.  I am aware of the n2k issue, but that doesn't seem to be the root here.  

I will try rad's suggestions and post back.
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by:JuusoConnecta
ID: 34146297
You have two seperate domains ? The internal Fully qualified domain name is the same for bouth of these new domains ?

yes / no ?

Thanks,
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by:mikeshaver
ID: 34146436
2 separate domains yes.  Internal FQDN is .local on the old one, and .com on the new one.

The issue has to be that the old server is somehow "remembering" the accounts that I have deleted/moved off that server as local accounts - which they no longer are.  I think its trying to deliver the emails locally to those accounts still.  
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by:markusdamenous
ID: 34146612
Can you post the actual error message that is received, so far not seen the full text.
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by:mikeshaver
ID: 34146764
Subject: to admin@mydomain.com
Sent: 11/15/2010 11:34 PM

The following recipient(s) could not be reached:

  Mike on 11/15/2010 11:34 PM
  The e-mail account does not exist at the organization this message was sent to. Check the e-mail address, or contact the recipient directly to find out the correct address.
  <exchange.mydomain.com #5.1.1>

"Exchange" is the OLD server.  Its internal name is exchange.mydomain.local.  
The NEW server is mail.mydomain.com (on a totally separate external IP).  

I tried to send this message from an existing account (different authorized domain than the one I moved) to an account that WAS on this server.  It appears the old server still thinks this is a local account?

The account I was sending to works fine from everywhere else, externally, internally on the new server.  Its just the OLD server is having issues mailing people that WERE on the old server.
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Assisted Solution

by:markusdamenous
markusdamenous earned 166 total points
ID: 34146836
Have you checked that the address book has updated correctly?  Thinking through the steps, possible that the address list has not updated on the server for some reason and therefore still giving an old address??
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by:mikeshaver
ID: 34147105
I removed the mailboxes as radhakrishnan2007 suggested.  No change.  Still getting the rejections.

As for the address book, from OWA connected to the old server, I went to the compose new email area, pressed the "to" field and tried to search the old addresses from the global address list and they are NOT found.  
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by:mikeshaver
ID: 34147153
Further to this suggestion:

"Also you have to check these setting .The name of the SMTP virtual server (Exch sys mgr / Admin groups / Site / Servers / email server / protocols / smtp  ... properties of server / Delivery Tab / Advanced button )  (or Exchange System Manager, Server, Expand your server, Protocols, SMTP,Default smtp virtual server, Properties, Delivery,Advanced button ) is an internal (to the company) dns name which must be different from the email server's external dns name.  You have to give a dns entry for it's external dns name.   So you needed to add a dns entry on the internet for it's internal name also.Or maybe the same entry you are using for your new server. "

Listed here is "Fully Qualified Domain name" which I have as: exchange.mydomain.COM  which is the correct external DNS name for the server.  The internal name of the server is exchange.mydomain.local

Should this .com be adjusted to .local?  

The MX records (external DNS) are different IP's for exchange.mydomain.com and mail.mydomain.com

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by:Radhakrishnan Rajayyan
ID: 34147792
Yes you can make it exchange.mydomain.com and also check the associated ptr record for that from your ISP end, Check the appropriate dns entry for the same.
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by:mikeshaver
ID: 34147800
It already is exchange.mydomain.com and the dns entry is correct at the ISP.  The server hasn't changed in years, except for me moving these accounts off recently.

I'm this close to just moving all the accounts and being done with it...
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Assisted Solution

by:JuusoConnecta
JuusoConnecta earned 167 total points
ID: 34152814
mikeshaver,

As a permanent workaround I would suggest you creating an SMTP connector from your exchange server 2003 which is located in the old domain, against exchange server 2010 which is located in your new domain, to have that specific mailtraffic go thru an "privat" smtp connector.

http://www.msexchange.org/tutorials/Using_SMTP_Connector_Internally.html
http://www.msexchange.org/tutorials/Configuring-SMTP-Connector.html
http://support.microsoft.com/kb/265293
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by:mikeshaver
ID: 34152843
Good ideas all (I like that one especially Juuso).  I decided to move all the accounts from the old server, manually, to the new server and all is well now.

I've divided up the points for everyone for all their help.

Mike
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