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Coexisting Exchange 2010 and 2003, users on 2010 can receive but cannot send

Posted on 2010-04-10
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HI
I Tried searching a lot and tried different settings only to mess up my current server......

Have an Exchange 2003 server. Works great and all email boxes are on that server.
Installed Exchange 2010 on another server,during install, it connected to the 2003 server and bought in all settings from that server. I moved 1 mailbox to 2010 and used Outlook 2003 to connect to it, can receive emails but cannot send internal or external.

I saw that no Send Connecter was created, I guess since it is a coexisting server and the 2003 server is sending emails out BUT i still created one with NO smart host (and later WITH smart host pointing to the 2003 IP checking with all the Authentications)
When I did that all emails for ALL USERS were going to the 2010 server and sitting in the "unreachable" folder. After I deleted this send connector and rebooted the server, emails for all users were going to the 2003 queue
I read about this intra-organization Send connector that should be there but i cannot find it or dont know where it should be.

So I am stummped, all help would be much appreciated
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Question by:gerriya3
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Expert Comment

by:Shreedhar Ette
ID: 30372001
Hi,

Refer this article:
http://technet.microsoft.com/en-us/library/dd638103.aspx

Hope this helps,
Shree
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Expert Comment

by:Glen Knight
ID: 30372160
When you install Exchange 2010 to coexist with 2003 the installation creates a routing group connector (you should be able to see this in Exchange System Manager on the 2003 server under connectors)

the send connector has nothingto do with mailflow between the Exchange servers.

On the 2003 server check that you don't have a smarthost configured on the Default SMTP Virtual Server which is located in Exchange System Manager under Administrative Groups > First Administrative Group > Servers > Servername > Protocols > SMTP
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Author Comment

by:gerriya3
ID: 30405828
thanks for the response guys
Shreedhar: thats the article I have already read which says "The Exchange 2010 Hub Transport servers use an implicit connector called the intra-organization Send connector to route messages between sites" .... where is this Intra-Organization Send Connector????

Demazter:Yes I do see the Connectors (in 2003 ESM) but i cannot modify its properties, gives me an error "ESM version 8.0.30535.0 or greater is required to edit this object. See about for version info."
About the Smart host, I do not see anything new under SMTP (only my smtp virtual server)

This is the first time I am doing a coexisting environment and I am sure I must have missed something during installation BUTWHAT ???

Any more ideas??
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Expert Comment

by:Glen Knight
ID: 30406636
Can you check the properties of the Virtual SMTP Server under the delivery tab and advanced.

Also check the port number is set to port 25?

Have a read of my blog post here: http://demazter.wordpress.com/2010/04/08/exchange-server-mailflow-during-migration/
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Author Comment

by:gerriya3
ID: 30410875
port is 25
in the advanced button :
max hop count : 30
mas domain: blank
fqdn: 2003 server name
smart host: blank
Perform reverse DNS lookup : unchecked

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Expert Comment

by:Glen Knight
ID: 30410943
just to clarify.

Is mail going from mailboxes on the 2003 server to the 2010 server?
Is mail going from mailboxes on the 2010 server to the 2003 server?
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Author Comment

by:gerriya3
ID: 30411435
yes mail is going from 2003 to 2010

no, mail is not going from 2010 to 2003

bottom line ... 2010 mailbox can receive from everybody (internal, external, 2003 server) but cannot send to anybody
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Expert Comment

by:Glen Knight
ID: 30411649
so, from the 2010 server can you telnet to the 2003 server on port 25?

so from a command prompt run:

telnet exchange_2003_IP_address 25

replace exchange_2003_IP_address with the IP address of your Exchange 2003 server.
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Author Comment

by:gerriya3
ID: 30413601
Yes, This is what I get

220 <2003server> Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Sun, 11 Apr 2010 11:00:46 -0400

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Expert Comment

by:Glen Knight
ID: 30413720
So when you try and send a message from a mailbox on the 2010 server to a user on the 2003 server what happens?

Do you get a Non Delivery Report or does it just disappear?  If you get an NDR can you post it please?
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Author Comment

by:gerriya3
ID: 30415907
When I send to an external address, it goes to 2010 and sits in Queue Viewer - Unreachable folder

When I send to a 2003 mailbox, I get the following

The following recipient(s) could not be reached:

      Tom on 4/11/2010 11:23 AM
            The message reached the recipient's e-mail system, but delivery was refused. Try resending the message. If delivery is refused again, contact the recipient directly.
            < #5.2.1>
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Author Comment

by:gerriya3
ID: 30416161
For the external address, after some time, I get the below
The following recipient(s) could not be reached:

      'Jessica' on 4/09/2010 2:17 PM
            Could not deliver the message in the time limit specified.  Please retry or contact your administrator.
            < #4.4.7 smtp;550 4.4.7 QUEUE.Expired; message expired in unreachable destination queue. Reason: A matching connector cannot be found to route the external recipient>
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Expert Comment

by:Glen Knight
ID: 30416789
Have you added an accepted domain to your Exchange 2010 install? That matches the domain you use on the 2003?

When you send externally you will use a Send connector if you haven't configured one under Organisation Configuration > Hub Transport then it will not go anywhere
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Expert Comment

by:Glen Knight
ID: 30416977
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Author Comment

by:gerriya3
ID: 30418200
Yes, I have a few Accepted Domains setup (Actually they all came from the 2003 server during the 2010 install)

About the Send Connector,
The NDR for external email makes sense to create a send conenctor but as I said in my first post, I initially did not see one (thinking maybe 2010 created one during install because it imported all other settings from the 2003 server) and hence tried to add one BUT after i added it, ALL USERS (2003 mailboxes) emails were going to the 2010 Queue (unreachable queue) and hence no emails were going out in the whole organization.
After i deleted the Send connector AND rebooted the2010  server, emails from 2003 mailboxes were going to the 2003 queue and going out.
I had kept the Cost as 1 though, do you think i should keep it higher...maybe 10....i will try messing with this

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Author Comment

by:gerriya3
ID: 30418687
what is scoped connector...should i check it?
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Accepted Solution

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Glen Knight earned 2000 total points
ID: 30418940
What address space did you give it? It should be *

also is there anything restricting port 25 on your network?
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