Moved from Exchange 2003 to 2010 Mail Relay and Others not working

This past month I setup a new Windows 2008 R2 server with Exchange 2010 and added it to our environment along with our old Server 2003 server running Exchange 2003.

I was able to get all of the mail boxes moved over and was able to verify that all the users where pointing to the new server, I was able to get all of the users sending and receiving e-mail without much hassle however I have several integrated systems that we have here and they are now broke.

I still have the old 2003 up and running and the hub transport is in place to the best of my knowledge. We have uptime and it still points to the old server by IP address which is still sending mail just fine. However our most important system is current not able to send any mail and is receiving an error in the code.

"The underlying connection was closed: Could not establish trust relationship for the SSL/TLS secure"

The program we use is developed in house and I am sure we could change all the code to the new server but right now thats not an option. The old server to the best of my knowledge is still allowing mail to flow so this should still work. Like I said my Up.Time is configured to point to the old server and if I send a report it goes through just fine.

This is from Up.Time to show you how its configured and working correctly
"Attempting to send message to up.time Administrator - **MASKED**@**MASKED**.com

Test message from up.time Monitoring Station

SMTP Server:
SMTP Port: 25
SMTP Sender: "uptime Monitoring Station" <uptime@**MASKED**>
SMTP Helo String:
SMTP User:

Message sent successfully."

I dont know if I need to enable the mail relay to certain IP's which is how its setup on the old server or if I should be looking into something else.


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burnersAuthor Commented:
I have seen those but what I don't get is the part about creating a new local interface address for the relay connector.

So lets say I want to allow to relay mail and my main IP of the server is, Do I have to add another IP to my local interface in the subnet? just to allow to relay?
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No, you can use the same ip address.
In your case both the servers are on different subnet, so you have to check if both and talk to each other.
You have to make a new receive connector:

expand server config. hub transport
add a new receive connector.
name it server by ip for example.
On the general tab use the fqdn for helo and ehlo responses.
on the network tab select all ip4 port 25 to receive mail.
select receive mail from servers that have these ip addresses. (make the list with ip adresses allowed relaying.)
Then on the permission groups tab select exchange servers
on the authentication tab select TLS and externally secured.

Done. conenctor to accept mail without authentication from a specified ip.
burnersAuthor Commented:
Actually I retract my original statement about mail being able to route through the old Exchange server.
It appears the messages I was looking at where from yesterday. So what I need is to get mail to continue to work when directed to the old server. The old server still has internet access and connects to the new server or should anyway.
burnersAuthor Commented:
I see now on the old server that there are TONS of e-mails stuck in the "Messages with an unreachable destination" folder.
Where should I start to get these unstuck?
check if your routing group connector is working.

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burnersAuthor Commented:
"check if your routing group connector is working."

On which server?
on yoour 2k3 server there must be a connection with your exchange servers.
burnersAuthor Commented:
I created a new routing group connector and mail started flowing :)
burnersAuthor Commented:
Very vague answer, no links to show a further description.
Sorry, i was in a hurry.  But i think you find out how :)
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